Standard Article

Rearrangements of Organozinc Compounds

Organozinc Compounds (2007)

  1. Varinder K. Aggarwal,
  2. Knut Sommer

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0376

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Aggarwal, V. K. and Sommer, K. 2009. Rearrangements of Organozinc Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Bristol, School of Chemistry, Cantock's Close, Bristol, United Kingdom

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

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Abstract

  • 1
    1,2-Metallate Rearrangements
  • 2
    Other Types of Rearrangements
  • 3
    Conclusions

Keywords:

  • organozinc compound rearrangement;
  • methylene homologations;
  • allylmetallation of alkenyl and alkynyl metals;
  • Reformatsky reaction;
  • methylene homologations in allene and olefin synthesis;
  • alkynyl metal allylmetallation;
  • Fritsch–Buttenberg–Wiechell rearrangement;
  • five-membered carbo- and heterocycles

Featured Compounds

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  1. 1 - 156
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4
Molecular Weight:190.671
Molecular Formula:C9H12ClLiSi
InChIKey:SPXSUKYDERDXSO-UHFFFAOYSA-N
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Compound 3
Molecular Weight:179.638
Molecular Formula:C8H18Zn
InChIKey:UQTVWGHDJHVLEP-UHFFFAOYSA-N
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5a
Molecular Weight:206.3993
Molecular Formula:C13H22Si
InChIKey:FIWVVVHDXJHYCM-UHFFFAOYSA-N
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9a
Molecular Weight:289.994
Molecular Formula:C10H10Br2
InChIKey:XPMWNSQZGXJDKS-UHFFFAOYSA-N
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10a
Molecular Weight:211.098
Molecular Formula:C10H11Br
InChIKey:HOSFCNKKWFRZGG-BQYQJAHWSA-N
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11a
Molecular Weight:188.3086
Molecular Formula:C14H20
InChIKey:RCPMKZJMEVYPBL-YFHOEESVSA-N
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:275.968
Molecular Formula:C9H8Br2
InChIKey:RRSAMRMQHHYSGN-QMMMGPOBSA-N
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Compound 15
Molecular Weight:382.642
Molecular Formula:C17H26BrLiZn
InChIKey:WLYWHZDTUMDUQV-USHJOAKVSA-N
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Compound 16
Molecular Weight:197.072
Molecular Formula:C9H9Br
InChIKey:IITYLOQJUHFLPM-IENPIDJESA-N
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Compound 17
Molecular Weight:174.282
Molecular Formula:C13H18
InChIKey:HJHWOPNCJJJNDB-ABLWVSNPSA-N
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Compound E-15
Molecular Weight:382.642
Molecular Formula:C17H26BrLiZn
InChIKey:WLYWHZDTUMDUQV-USHJOAKVSA-N
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Compound Z-17
Molecular Weight:174.282
Molecular Formula:C13H18
InChIKey:HJHWOPNCJJJNDB-STQMWFEESA-N
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Compound E-17
Molecular Weight:174.282
Molecular Formula:C13H18
InChIKey:HJHWOPNCJJJNDB-OLZOCXBDSA-N
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Compound E-18
Molecular Weight:231.517
Molecular Formula:C9H8BrCl
InChIKey:PGTIHSHVZGIQIK-IUCAKERBSA-N
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28a
Molecular Weight:238.303
Molecular Formula:C12H14O3S
InChIKey:JNLAVHWVWMEYCU-UHFFFAOYSA-N
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31a
Molecular Weight:201.3255
Molecular Formula:C15H20
InChIKey:Not Available
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Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32a
Molecular Weight:201.3255
Molecular Formula:C15H20
InChIKey:Not Available
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Compound 33
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40
Molecular Weight:333.245
Molecular Formula:CH2I2Zn
InChIKey:IVHZANOQGCIPSI-UHFFFAOYSA-M
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 52
Molecular Weight:353.577
Molecular Formula:C12H17IZn
InChIKey:GWLOUCOURPVRFX-UHFFFAOYSA-N
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Compound 47a
Molecular Weight:164.224
Molecular Formula:C9H8OS
InChIKey:UUBXCGJXEGMPMI-LLVKDONJSA-N
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Compound 48a
Molecular Weight:284.884
Molecular Formula:C13H17CuOS
InChIKey:HBCKHHYOHJRNHQ-RSAXXLAASA-N
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Compound 54
Molecular Weight:152.2765
Molecular Formula:C11H20
InChIKey:OQQGYZZPAZFAIA-LLVKDONJSA-N
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Compound 55
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 64
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 65a
Molecular Weight:160.182
Molecular Formula:C10H17LiO
InChIKey:MIWRLGSVFFECJQ-UHFFFAOYSA-N
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Compound 66
Molecular Weight:416.345
Molecular Formula:C21H40ClLiOZn
InChIKey:RMJOJWNJJFYMFE-UHFFFAOYSA-N
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Compound 67
Molecular Weight:373.951
Molecular Formula:C21H40OZn
InChIKey:NTXNMAYCBXAMHK-UHFFFAOYSA-N
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Compound 65
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 69
Molecular Weight:186.385
Molecular Formula:C3H5BrZn
InChIKey:UZNJLSDYFXAQJJ-UHFFFAOYSA-M
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Compound 70
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Z-68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70a
Molecular Weight:304.531
Molecular Formula:C11H20BrLiZn
InChIKey:TWILTKJTCAMTBB-UHFFFAOYSA-M
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Compound syn-73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound anti-73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72c
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound anti-77
Molecular Weight:154.2924
Molecular Formula:C11H22
InChIKey:TVMWQEWTHQMCOX-WDEREUQCSA-N
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Compound Z-75
Molecular Weight:104.119
Molecular Formula:C7H13Li
InChIKey:MRJGOCKJYGVRIS-UHFFFAOYSA-N
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Compound 78
Molecular Weight:282.1617
Molecular Formula:C10H19IO
InChIKey:WLEJPTUZIMGBPE-FPLPWBNLSA-N
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Compound 80
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:MOJUXTLYFXTZMC-BDAKNGLRSA-N
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Compound 81
Molecular Weight:268.528
Molecular Formula:C9H15BrZn
InChIKey:MNBANKRJHBNDDD-BPRGXCPLSA-M
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Compound 83
Molecular Weight:228.0282
Molecular Formula:C5H9IO2
InChIKey:WAOPQEDNWXARIN-IHWYPQMZSA-N
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Compound 85
Molecular Weight:226.449
Molecular Formula:C6H9BrZn
InChIKey:BDVZPUOEXQMUAO-UHFFFAOYSA-M
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Compound 86
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 87
Molecular Weight:208.0401
Molecular Formula:C6H9I
InChIKey:OJKOQKONADNFKT-PLNGDYQASA-N
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Compound anti-88
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:OUDNTEVXUNFGQW-BDAKNGLRSA-N
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Compound syn-88
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:OUDNTEVXUNFGQW-IUCAKERBSA-N
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Compound 89
Molecular Weight:215.414
Molecular Formula:C8H15BrMg
InChIKey:WBNDFDLJYMZWKJ-UHFFFAOYSA-M
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Compound anti-91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound anti-92
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:GAOITISVHXTHOU-OLZOCXBDSA-N
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Compound syn-91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound syn-92
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:GAOITISVHXTHOU-STQMWFEESA-N
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Compound 94a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 93b
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:AVUCPXPFLJVXIP-UHFFFAOYSA-N
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Compound 96b
Molecular Weight:242.3544
Molecular Formula:C14H26O3
InChIKey:GDNFOLVRSIUWCV-TZMCWYRMSA-N
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Compound 95b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 93a
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:GFUMIIXNZURYNB-UHFFFAOYSA-N
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Compound 65b
Molecular Weight:192.181
Molecular Formula:C10H17LiO3
InChIKey:YZQWIKXDUUGNSQ-UHFFFAOYSA-N
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Compound 93
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 95
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 95a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 96
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 96a
Molecular Weight:210.3556
Molecular Formula:C14H26O
InChIKey:PZGSSELADZZQJT-DGCLKSJQSA-N
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Compound 97
Molecular Weight:179.187
Molecular Formula:C12H14LiN
InChIKey:UPMLTAMLJKUVJA-RFVHGSKJSA-N
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Compound 98
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 99
Molecular Weight:243.3871
Molecular Formula:C17H25N
InChIKey:YWKIRBLHJWWIOF-BZSJEYESSA-N
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Compound 100
Molecular Weight:243.3871
Molecular Formula:C17H25N
InChIKey:WIGNVGFDBMMDHA-GDBMZVCRSA-N
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Compound 102
Molecular Weight:220.371
Molecular Formula:C5H8BrLiZn
InChIKey:AEYPXSRGINFNEA-UHFFFAOYSA-M
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Compound 104
Molecular Weight:220.371
Molecular Formula:C5H8BrLiZn
InChIKey:RXOSUZDFQPZYBS-UHFFFAOYSA-M
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Compound 105
Molecular Weight:400.578
Molecular Formula:C15H24Zn3
InChIKey:BLKMMOVZZSUEMA-UHFFFAOYSA-N
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Compound 110
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 111
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:NBJRAJBHOOBBLK-UHFFFAOYSA-N
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Compound 112a
Molecular Weight:223.359
Molecular Formula:C15H26O
InChIKey:CZTKWCRAIPRKHI-UHFFFAOYSA-N
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Compound 112b
Molecular Weight:223.359
Molecular Formula:C15H26O
InChIKey:CZTKWCRAIPRKHI-UHFFFAOYSA-N
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Compound 113
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 113a
Molecular Weight:208.3398
Molecular Formula:C14H24O
InChIKey:OEQJBFWOUOPVDU-CHWSQXEVSA-N
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Compound 113b
Molecular Weight:240.3386
Molecular Formula:C14H24O3
InChIKey:ADASCGOXHPMEDP-ZIAGYGMSSA-N
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Compound 115-Li
Molecular Weight:186.295
Molecular Formula:C11H19LiSi
InChIKey:FWGBUWVLBONHIN-UHFFFAOYSA-N
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Compound 115-MgBr
Molecular Weight:283.563
Molecular Formula:C11H19BrMgSi
InChIKey:RYZWNCYOZNXOKB-UHFFFAOYSA-M
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Compound 117
Molecular Weight:180.362
Molecular Formula:C11H20Si
InChIKey:CMXDOPLCXGTGLR-GHMZBOCLSA-N
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Compound 118
Molecular Weight:306.2585
Molecular Formula:C11H19ISi
InChIKey:JFUUXLDDVJCYJR-MNOVXSKESA-N
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Compound 119
Molecular Weight:220.4259
Molecular Formula:C14H24Si
InChIKey:ZFZKNTURMBXHKW-ZIAGYGMSSA-N
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Compound 114
Molecular Weight:180.362
Molecular Formula:C11H20Si
InChIKey:VPDUOUQZMQFMKH-UHFFFAOYSA-N
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Compound 116
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 120
Molecular Weight:324.667
Molecular Formula:C11H19BrSiZn
InChIKey:KEXWSLXOAUOQHW-UHFFFAOYSA-M
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Compound 116-ZnBr
Molecular Weight:324.667
Molecular Formula:C11H19BrSiZn
InChIKey:WJQJWXUTRXIMGB-IUDGJIIWSA-M
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Compound 121
Molecular Weight:304.5423
Molecular Formula:C19H32OSi
InChIKey:XFAYTGUMEDEJKB-QZTJIDSGSA-N
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Compound 122
Molecular Weight:304.5423
Molecular Formula:C19H32OSi
InChIKey:CHAXNOAACQUHBC-OFLQAFCJSA-N
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Compound 123
Molecular Weight:376.3484
Molecular Formula:C15H25IOSi
InChIKey:RXQFMRCDHODAOP-UONOGXRCSA-N
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Compound 124
Molecular Weight:271.4726
Molecular Formula:C17H25NSi
InChIKey:SSPDKWFCXCJBSP-NVXWUHKLSA-N
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Compound 125
Molecular Weight:397.3691
Molecular Formula:C17H24INSi
InChIKey:PCRVWMSDWXWQIP-DLBZAZTESA-N
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Compound 127
Molecular Weight:301.515
Molecular Formula:C8H14BrNO2Zn
InChIKey:WCRUNSLSOIEHIC-MIIBGCIDSA-L
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Compound 128
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:BLGAZAQFPAZSJX-RQJHMYQMSA-N
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Compound 129
Molecular Weight:283.1067
Molecular Formula:C8H14INO2
InChIKey:UMSBAHXGWBRSEL-BQBZGAKWSA-N
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Compound 130
Molecular Weight:197.2741
Molecular Formula:C11H19NO2
InChIKey:RLILZUGJQMIRGC-ZJUUUORDSA-N
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Compound 126
Molecular Weight:163.143
Molecular Formula:C8H14LiNO2
InChIKey:FSWHIQABGRTVJN-CFYXSCKTSA-M
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Compound 131
Molecular Weight:214.115
Molecular Formula:C6H13ClSiZn
InChIKey:YYRWOWREOYSPGN-UHFFFAOYSA-M
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Compound 132
Molecular Weight:214.115
Molecular Formula:C6H13ClSiZn
InChIKey:DGLNKFUYECFKJA-UHFFFAOYSA-M
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Compound 133
Molecular Weight:228.4033
Molecular Formula:C12H24O2Si
InChIKey:NLNINYWSRIQPBH-HTAVTVPLSA-N
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Compound 134
Molecular Weight:228.4033
Molecular Formula:C12H24O2Si
InChIKey:VEDQMFDWUTVHCF-MCIGGMRASA-N
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Compound 136
Molecular Weight:214.115
Molecular Formula:C6H13ClSiZn
InChIKey:PTKRTLYZZALHDW-UHFFFAOYSA-M
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