Standard Article

Recent Advances in the Insertion and Extrusion Reactions of Selenium and Tellurium in Organic Compounds

Organic Selenium and Tellurium (2013)

  1. Frank S. Guziec, Jr.,
  2. Lynn James Guziec

Published Online: 18 MAR 2013

DOI: 10.1002/9780470682531.pat0712

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

S. Guziec,, F. and James Guziec, L. 2013. Recent Advances in the Insertion and Extrusion Reactions of Selenium and Tellurium in Organic Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. Department of Chemistry and Biochemistry, Southwestern University, Georgetown, TX 78626, USA. Fax: (512)863-1969; e-mail: guziecf@southwestern.edu and guziecl@southwestern.edu

Publication History

  1. Published Online: 18 MAR 2013

Chemistry Terms

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Abstract

Insertion and extrusion reactions are common transformations in organoselenium and—tellurium chemistry. These processes are often synthetically useful, allowing for the preparation of molecules difficult or impossible to prepare using other methods. Insertion reactions involve the chemical insertion of an atom between two directly bonded atoms in a molecule, forming two new bonds. Extrusion reactions are generally the reverse of the insertion process, removing an atom and forming a bond between the atoms to which it was previously bonded. Twofold extrusion reactions involve loss of two atoms from a cyclic system affording a doubly bonded product. Eliminations of an atom from a bicyclic or cyclic system affording a diene, polyene or aromatic compound are also termed extrusion reactions. This chapter will primarily cover selenium and tellurium insertions into carbon-metal and metal-metal bonds, as well as some other non-conventional insertion reactions. Insertion reactions involving directed metalation andinsertions into metallocenes are also described. Extrusion reactions affording carbon-carbon bonds, carbon-metal bonds, and other non-metal to metal bonds, as well as twofold extrusions are also covered. The synthetic utility of these reactions is also described.

Keywords:

  • insertion;
  • extrusion;
  • heterocycles;
  • organometallic;
  • organolithium;
  • directed metalation;
  • metallocene;
  • twofold extrusion;
  • porphyrin;
  • fullerene

Featured Compounds

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  1. 1 - 146
Compound 1
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 2
Molecular Weight:221.98
Molecular Formula:C4H9LiSe2
InChIKey:IXIWWTZAFJQEAP-UHFFFAOYSA-M
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Compound 3
Molecular Weight:393.4
Molecular Formula:C10H18Te2
InChIKey:NHYKLYMQDBEVAX-UHFFFAOYSA-N
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Compound 4
Molecular Weight:375.34
Molecular Formula:C18H29LiN2OSe
InChIKey:AINSNADVDRDBER-UHFFFAOYSA-M
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Compound 5
Molecular Weight:370.34
Molecular Formula:C28H20Li2
InChIKey:IZRFXVOAGBNGOA-UHFFFAOYSA-N
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Compound 6
Molecular Weight:443.16
Molecular Formula:C16H14Se3
InChIKey:YIBLYHUTSBIEIQ-QXMHVHEDSA-N
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Compound 7
Molecular Weight:364.2
Molecular Formula:C16H14Se2
InChIKey:PHDCMCUPWJWCDG-QXMHVHEDSA-N
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Compound 8
Molecular Weight:522.12
Molecular Formula:C16H14Se4
InChIKey:BJZVUOCUNGWIEC-QXMHVHEDSA-N
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Compound 9
Molecular Weight:295.1
Molecular Formula:C2H2Li2Te2
InChIKey:BJINFFMATKHNOA-UAIGNFCESA-L
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Compound 10
Molecular Weight:586.5
Molecular Formula:C6H4Te4
InChIKey:ZAXIAHSDEGYBLJ-UHFFFAOYSA-N
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Compound 11
Molecular Weight:1000.9
Molecular Formula:C38H32P2PtTe2
InChIKey:JTYORWKPYRESBA-KWZUVTIDSA-L
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Compound 12
Molecular Weight:335.2
Molecular Formula:C5H6Li2Te2
InChIKey:DGKDXSGOUGKOOL-UHFFFAOYSA-L
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Compound 13
Molecular Weight:666.6
Molecular Formula:C12H12Te4
InChIKey:SGBKGXLBEGFMJB-UHFFFAOYSA-N
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Compound 14
Molecular Weight:209.099
Molecular Formula:C13H9Li2NO
InChIKey:UBTWDJAZOGNIBN-UHFFFAOYSA-M
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15a
Molecular Weight:288.06
Molecular Formula:C13H9Li2NOSe
InChIKey:XMTZBWFOSOZCIV-UHFFFAOYSA-L
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Compound 15b
Molecular Weight:336.7
Molecular Formula:C13H9Li2NOTe
InChIKey:PKBCENJCOUXWJD-UHFFFAOYSA-L
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Compound 16a
Molecular Weight:290.22
Molecular Formula:C14H13NOSe
InChIKey:DYAVFTICFASTKQ-UHFFFAOYSA-N
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Compound 16b
Molecular Weight:338.9
Molecular Formula:C14H13NOTe
InChIKey:MTANVWRIBKJCQL-UHFFFAOYSA-N
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Compound 17
Molecular Weight:274.18
Molecular Formula:C13H9NOSe
InChIKey:DYEFUKCXAQOFHX-UHFFFAOYSA-N
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Compound 18
Molecular Weight:550.37
Molecular Formula:C26H20N2O2Se2
InChIKey:FTRFOFPAMKYZPH-UHFFFAOYSA-N
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Compound 19
Molecular Weight:359.3
Molecular Formula:C13H10ClNOTe
InChIKey:LDXOIQDWLRITMB-UHFFFAOYSA-N
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Compound 20
Molecular Weight:403.7
Molecular Formula:C13H10BrNOTe
InChIKey:KDQMNANACBNHLQ-UHFFFAOYSA-N
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Compound 21
Molecular Weight:450.7
Molecular Formula:C13H10INOTe
InChIKey:OBJWQHXOESUBHM-UHFFFAOYSA-N
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Compound 22
Molecular Weight:647.6
Molecular Formula:C26H20N2O2Te2
InChIKey:UOEWIEZNPOUIDK-UHFFFAOYSA-N
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Compound 23
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 25
Molecular Weight:88.037
Molecular Formula:C4H5LiN2
InChIKey:PGGUIZNCKIWWBO-UHFFFAOYSA-N
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Compound 26
Molecular Weight:161.06
Molecular Formula:C4H6N2Se
InChIKey:CACMOFJOXKRQIJ-UHFFFAOYSA-N
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Compound 27
Molecular Weight:114.169
Molecular Formula:C4H6N2S
InChIKey:PMRYVIKBURPHAH-UHFFFAOYSA-N
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Compound 28
Molecular Weight:265.21
Molecular Formula:C12H14N2Se
InChIKey:GYTIOBJOEGSURT-UHFFFAOYSA-N
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Compound 29
Molecular Weight:237.16
Molecular Formula:C10H10N2Se
InChIKey:FAWMRHVTDMIFQM-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 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31a
Molecular Weight:258.9
Molecular Formula:C2H3BrMgTe
InChIKey:UQCSSTSKCWKSJS-UHFFFAOYSA-L
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Compound 31b
Molecular Weight:272.9
Molecular Formula:C3H5BrMgTe
InChIKey:JSLRFVZDQXFPJD-BGQPXYRPSA-L
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Compound 31c
Molecular Weight:272.9
Molecular Formula:C3H5BrMgTe
InChIKey:PVVGZMPBCQIRON-UHFFFAOYSA-L
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Compound 31d
Molecular Weight:335
Molecular Formula:C8H7BrMgTe
InChIKey:NCTMROSTLUSBCP-AQTVDGORSA-L
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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 36
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 33a
Molecular Weight:210.21
Molecular Formula:C2H3BrMgSe
InChIKey:QASSDSUYPYTCPO-UHFFFAOYSA-L
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Compound 33b
Molecular Weight:224.24
Molecular Formula:C3H5BrMgSe
InChIKey:LNMRKFKWOBRXNU-WTVBWJGASA-L
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Compound 33c
Molecular Weight:224.24
Molecular Formula:C3H5BrMgSe
InChIKey:LNMRKFKWOBRXNU-BGQPXYRPSA-L
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Compound 33d
Molecular Weight:238.27
Molecular Formula:C4H7BrMgSe
InChIKey:BQMDAOSBXVXNTP-UHFFFAOYSA-L
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Compound 36a
Molecular Weight:155.7
Molecular Formula:C2H4Te
InChIKey:DFBZWBQFMVUQHX-UHFFFAOYSA-N
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Compound 36b
Molecular Weight:183.7
Molecular Formula:C4H8Te
InChIKey:FDGGDMGWOGQDTQ-UHFFFAOYSA-N
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Compound 36c
Molecular Weight:169.7
Molecular Formula:C3H6Te
InChIKey:PYTBQISGFSWKDL-UHFFFAOYSA-N
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Compound 37
Molecular Weight:198.4203
Molecular Formula:C12H26Si
InChIKey:PZPSUANGKSNRSG-NXEZZACHSA-N
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Compound 38
Molecular Weight:277.38
Molecular Formula:C12H26SeSi
InChIKey:FABBGSNCCQDPGK-NXEZZACHSA-N
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Compound 39
Molecular Weight:356.34
Molecular Formula:C12H26Se2Si
InChIKey:PJLYBGNNHQJEJI-NXEZZACHSA-N
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Compound 40
Molecular Weight:210.431
Molecular Formula:C13H26Si
InChIKey:VWXBIUOTTPOBHV-UHFFFAOYSA-N
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Compound 41
Molecular Weight:368.35
Molecular Formula:C13H26Se2Si
InChIKey:BKDNFTGBEXXOKV-MNOVXSKESA-N
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Compound 42
Molecular Weight:224.4576
Molecular Formula:C14H28Si
InChIKey:GPLNMQGTZICJEB-UHFFFAOYSA-N
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Compound 43
Molecular Weight:382.38
Molecular Formula:C14H28Se2Si
InChIKey:WPCRLGOWRXSZSK-NEPJUHHUSA-N
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Compound 44
Molecular Weight:303.42
Molecular Formula:C14H28SeSi
InChIKey:LPAXXTDIEBGLNU-VXGBXAGGSA-N
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Compound 45
Molecular Weight:525.7
Molecular Formula:C16H14Br2O2Te
InChIKey:HXFLJDMBBVAJDG-UHFFFAOYSA-N
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Compound 46
Molecular Weight:497.5
Molecular Formula:C4H8I2N2O2Te
InChIKey:WXILLKIXMCWKBW-UHFFFAOYSA-N
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Compound 47
Molecular Weight:306.2723
Molecular Formula:C17H10N2O4
InChIKey:ZOYYKFHOBNBFHE-UHFFFAOYSA-N
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Compound 49
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 52
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53
Molecular Weight:594
Molecular Formula:C22H37MnO3P2Te
InChIKey:JNLTVBSYBZVRQV-UHFFFAOYSA-M
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Compound 54
Molecular Weight:517.9
Molecular Formula:C16H33MnO3P2Te
InChIKey:NBJZOCZZZYXTFL-UHFFFAOYSA-M
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 57
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 59
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:758.4
Molecular Formula:C40H60Sc2Te
InChIKey:ZCBCDACMOGEHIJ-UHFFFAOYSA-N
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Compound 62
Molecular Weight:317.4222
Molecular Formula:C20H31Sc
InChIKey:Not Available
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Compound 63
Molecular Weight:1197
Molecular Formula:C42H102Li2O6Si8Te2
InChIKey:PDLHXXJHQJOZDI-UHFFFAOYSA-N
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Compound 64
Molecular Weight:750.5
Molecular Formula:C18H54Si8Te2
InChIKey:KDICFWANMAVBKI-UHFFFAOYSA-N
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Compound 65
Molecular Weight:376.3
Molecular Formula:C9H28Si4Te
InChIKey:BHDUFNKDZIHJES-UHFFFAOYSA-N
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Compound 66
Molecular Weight:250.5409
Molecular Formula:C9H27PSi3
InChIKey:OUMZKMRZMVDEOF-UHFFFAOYSA-N
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Compound 67
Molecular Weight:487.42
Molecular Formula:C9H27PSe3Si3
InChIKey:GGOQOCAHGOKQCE-UHFFFAOYSA-N
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Compound 68
Molecular Weight:670.54
Molecular Formula:C12H36P2Se4Si4
InChIKey:UPWKWUKBRPAXEM-UHFFFAOYSA-N
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Compound 69
Molecular Weight:1034.769
Molecular Formula:C50H44Cl2P4Pt
InChIKey:NFVKFBIAQCCCDV-UHFFFAOYSA-L
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Compound 70
Molecular Weight:1419.92
Molecular Formula:C52H46F6O6P4PtS2Se2
InChIKey:RVOPDRDPRRFASU-UHFFFAOYSA-L
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Compound 71
Molecular Weight:1405.9
Molecular Formula:C51H44F6O6P4PtS2Se2
InChIKey:FMPJPGSSFPDRMK-UHFFFAOYSA-L
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 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 75
Molecular Weight:843.48
Molecular Formula:C24H48Co2Se2Si4Sn
InChIKey:KJZZYNNYIBLXAH-UHFFFAOYSA-N
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Compound 76
Molecular Weight:1077.99
Molecular Formula:C33H81CoSeSi8Sn2
InChIKey:MVCPVZDVSQSRFH-UHFFFAOYSA-N
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Compound 77
Molecular Weight:427.274
Molecular Formula:C27H33Ga
InChIKey:XIAWAISWRNWEQP-UHFFFAOYSA-N
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Compound 78
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 83
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 84
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 91
Molecular Weight:1576.19
Molecular Formula:C90H138Sn3
InChIKey:CHJAVRXYLATBDT-UHFFFAOYSA-N
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Compound 92
Molecular Weight:1050.79
Molecular Formula:C60H92Sn2
InChIKey:ORQBPKXJMBKUTE-UHFFFAOYSA-N
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Compound 85
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86a
Molecular Weight:611.87
Molecular Formula:C36H44SeSi2
InChIKey:GIYLZCGDXCQAMP-UHFFFAOYSA-N
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Compound 86b
Molecular Weight:660.5
Molecular Formula:C36H44Si2Te
InChIKey:FYZIEDAHMBFOLO-UHFFFAOYSA-N
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Compound 87
Molecular Weight:678.12
Molecular Formula:C40H52Ge2
InChIKey:IFXCBFYKIBCAHR-UHFFFAOYSA-N
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Compound 88
Molecular Weight:805.7
Molecular Formula:C40H52Ge2Te
InChIKey:DIPSMHOKOQFNBI-UHFFFAOYSA-N
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Compound 89
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 90
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 93
Molecular Weight:848.2
Molecular Formula:C60Te
InChIKey:KUXOZVPRXZCALN-UHFFFAOYSA-N
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Compound 94
Molecular Weight:404.37
Molecular Formula:C22H19N3Se
InChIKey:AELOEKNGIJKJTQ-FCQUAONHSA-N
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Compound 95
Molecular Weight:325.4064
Molecular Formula:C22H19N3
InChIKey:HZKBAKPKMSQPAH-UHFFFAOYSA-N
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Compound 97
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 98
Molecular Weight:295.2
Molecular Formula:C12H12N2O2Se
InChIKey:BCGROJSINLAGCV-UHFFFAOYSA-N
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Compound 99
Molecular Weight:413.41
Molecular Formula:C20H30O4Se
InChIKey:GXZFZLBZEOBGPX-UHFFFAOYSA-N
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Compound 100
Molecular Weight:334.4498
Molecular Formula:C20H30O4
InChIKey:YRVVDLYYLPYOGM-UHFFFAOYSA-N
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Compound 101
Molecular Weight:270.3263
Molecular Formula:C16H18N2O2
InChIKey:WVXWESPTNWETRJ-UHFFFAOYSA-N
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Compound 102
Molecular Weight:443.16
Molecular Formula:C16H14Se3
InChIKey:YIBLYHUTSBIEIQ-QXMHVHEDSA-N
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Compound 103
Molecular Weight:364.2
Molecular Formula:C16H14Se2
InChIKey:PUEJUYUFIJNYRH-HOTGVXAUSA-N
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Compound 104
Molecular Weight:364.2
Molecular Formula:C16H14Se2
InChIKey:PHDCMCUPWJWCDG-QXMHVHEDSA-N
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Compound 106
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 108
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 109
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 110
Molecular Weight:285.2
Molecular Formula:C14H10N2Se
InChIKey:YMRXGZVSRMTEOK-UHFFFAOYSA-N
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Compound 111
Molecular Weight:400.33
Molecular Formula:C23H15NOSe
InChIKey:MWJJGSSZDQJWII-UHFFFAOYSA-N
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Compound 112
Molecular Weight:463.4807
Molecular Formula:C29H21NO5
InChIKey:VZBAJNSZYSYAPV-UHFFFAOYSA-N
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Compound 113
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 114
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 115
Molecular Weight:286.8
Molecular Formula:C10H9NOTe
InChIKey:SIVGVHNXBDHPRD-UHFFFAOYSA-N
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Compound 116
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 117
Molecular Weight:629.7902
Molecular Formula:C46H35N3
InChIKey:ARIHQYRIJGQYJS-RZQFIFLUSA-N
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Compound 116a
Molecular Weight:755.4
Molecular Formula:C46H33N3Te
InChIKey:OMKBPUHOOCKXNT-VXBCHASASA-N
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Compound 118
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 119
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 120
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 116b
Molecular Weight:817.3
Molecular Formula:C44H27N5O4Te
InChIKey:LLAZPSKVDXATOG-JAAFTSFNSA-N
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Compound 119a
Molecular Weight:771.4
Molecular Formula:C46H33N3OTe
InChIKey:AHDVXICACUFYBN-VXBCHASASA-N
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Compound 119b
Molecular Weight:833.3
Molecular Formula:C44H27N5O5Te
InChIKey:XNXCOKHIJJRBIG-JAAFTSFNSA-N
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Compound 120a
Molecular Weight:643.7737
Molecular Formula:C46H33N3O
InChIKey:QETRBTFSXFYPNU-VXBCHASASA-N
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Compound 120b
Molecular Weight:705.7157
Molecular Formula:C44H27N5O5
InChIKey:FMMFDZXVBHAZHE-JAAFTSFNSA-N
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Compound 121
Molecular Weight:337.4
Molecular Formula:C19H30Se
InChIKey:SXLZPSJMVHJBJT-UHFFFAOYSA-N
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Compound 123
Molecular Weight:384.6807
Molecular Formula:C28H48
InChIKey:QXUYMZKQIOVSEP-UHFFFAOYSA-N
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Compound 124
Molecular Weight:500.1
Molecular Formula:C26H32N2Te
InChIKey:GRQMOHANJIDTDS-UHFFFAOYSA-N
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Compound 125
Molecular Weight:344.5323
Molecular Formula:C26H32
InChIKey:DETSIKVIFORADW-UHFFFAOYSA-N
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Compound 126
Molecular Weight:451.51
Molecular Formula:C26H32N2Se
InChIKey:QHEUSJNDSAMAJK-UHFFFAOYSA-N
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Compound 127
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 128
Molecular Weight:217.3498
Molecular Formula:C15H23N
InChIKey:RVMZSLSYWTVUIJ-UHFFFAOYSA-N
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Compound 129
Molecular Weight:1279.7
Molecular Formula:C50H44P4PtSe4
InChIKey:YOFXHYNAIHHVLO-UHFFFAOYSA-N
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