Standard Article

5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane

  1. Stuart J. Mahoney,
  2. Eric Fillion

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01600

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Mahoney, S. J. and Fillion, E. 2013. 5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. University of Waterloo, Waterloo, Ontario, Canada

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

original image

(5-Chloro-1-aza-5-stannabicyclo[3.3.3]undecane)

[93253-73-7] C9H18ClNSn (MW 294.41)

InChI = 1S/C9H18N.ClH.Sn/c1-4-7-10(8-5-2)9-6-3;;/h1-9H2;1H;/q;;+1/p-1

InChIKey = BRPCJQRIZVVNKX-UHFFFAOYSA-M

(precursor to organostannatranes that enable facile transfer of apical group due to intramolecular activation; selective alkyl transfer agent precursor)

Alternate Name: 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane.

Physical Data: mp 236–238 °C (EtOH),1 222–224 °C (MeOH).2

Solubility: soluble in Et2O, THF, EtOAc, CH2Cl2, and hexanes; slightly soluble in MeCN, MeOH, and i-PrOH; insoluble in H2O and aq. HCl.

Form Supplied in: commercially available solid.

Analysis of Reagent Purity:13C and 119Sn NMR.3

Preparative Methods: initially prepared by transmetalation of N(CH2CH2CH2MgCl)34, 5 with SnCl4 in 12–15% yield. Subsequently, hydrozirconation of N(CH2CH–CH2)3 with Cp2ZrHCl followed by transmetalation with SnCl4 furnished 5-chloro-1-aza-5-stannabicyclo[3.3.3]undecane in 50% yield.2 Alternatively, 5-chloro-1-aza-5-stannabicyclo[3.3.3]undecane is prepared in 40% yield from N(CH2CH2CH2SnMe3)3 by thermal redistribution with Me2SnCl2.1, 5 N(CH2CH2CH2SnMe3)3 is synthesized by reacting N(CH2CH2CH2Cl)3 with Me3SnNa in liquid ammonia at −78 °C. Drawbacks to the preparation of chlorostannatrane by these routes are low yields, handling of volatile methyltin derivatives, harsh conditions, and/or expensive reagents.

A scalable, two-step synthesis that remedies the former issues consists of the thermal redistribution of N(CH2CH2CH2SnBu3)3 with SnCl4 (eq 1). The tributylstannane N(CH2CH2CH2SnBu3)3 is accessible in 66% yield by the Pd/Al2O3-catalyzed hydrostannation of N(CH2CH[DOUBLE BOND]CH2)3 with Bu3SnH, or alternatively, by the substitution of N(CH2CH2CH2Cl)3 with Bu3SnLi in 78% yield.6

original image(1)

Purification: acid/base extraction6 or recrystallization from MeOH.2

Handling, Storage, and Precautions: toxic by ingestion and is a skin, eye, and respiratory tract irritant.7

Featured Compounds

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  1. 1 - 66
Compound Information
Molecular Weight:294.41
Molecular Formula:C9H18ClNSn
InChIKey:BRPCJQRIZVVNKX-UHFFFAOYSA-M
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Compound Information
Molecular Weight:1010.4
Molecular Formula:C45H99NSn3
InChIKey:DXMBSKDNNDAYDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.52
Molecular Formula:Cl4Sn
InChIKey:Not Available
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:345.76
Molecular Formula:C9H18BF4NSn
InChIKey:DVCYQCOXYAVOOK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.673
Molecular Formula:AgBF4
InChIKey:CCAVYRRHZLAMDJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
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Compound Information
Molecular Weight:273.99
Molecular Formula:C10H21NSn
InChIKey:WQHUTROLEJVBSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.8355
Molecular Formula:CH2I2
InChIKey:NZZFYRREKKOMAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:399.89
Molecular Formula:C10H20INSn
InChIKey:NHFOZRIZUUXPNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.531
Molecular Formula:C4H10Zn
InChIKey:HQWPLXHWEZZGKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.034
Molecular Formula:C7H7BrO
InChIKey:QJPJQTDYNZXKQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:CHLICZRVGGXEOD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1155.56
Molecular Formula:C72H60P4Pd
InChIKey:NFHFRUOZVGFOOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.07
Molecular Formula:C13H27NSn
InChIKey:IFRSOWRLHKIOQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:PRBLRGZSVKMPDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:346.17
Molecular Formula:C13H29NSiSn
InChIKey:KZCGJFNFAHUBRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3455
Molecular Formula:C11H18OSi
InChIKey:YZNOHWUDLGWICS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.076
Molecular Formula:C8H10BrN
InChIKey:XYZWMVYYUIMRIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:Not Available
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:PJCNYQIIQZWBGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:207.3873
Molecular Formula:C12H21NSi
InChIKey:QYAOXGQPWIXJNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.005
Molecular Formula:C6H4BrNO2
InChIKey:FWIROFMBWVMWLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.128
Molecular Formula:C7H7NO2
InChIKey:BLZZCTFVJUMNBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:INMYTBBXRJWIOA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:209.3171
Molecular Formula:C10H15NO2Si
InChIKey:SPCDGPYEEJJPAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.0826
Molecular Formula:C7H13I
InChIKey:XULQQNDHGTXWAD-VOTSOKGWSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:ILPBINAXDRFYPL-HWKANZROSA-N
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Compound Information
Molecular Weight:365.89
Molecular Formula:C6H10Cl2Pd2
InChIKey:OTBRMLNJALKXGN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:259.43
Molecular Formula:C4H6Cl2N2Pd
InChIKey:RBYGDVHOECIAFC-UHFFFAOYSA-L
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:972.62
Molecular Formula:C32H47F6N5O9S3Sn
InChIKey:GDPJRGZXJNAUCC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:1173.255
Molecular Formula:C46H60F6N6O15S3Si
InChIKey:JDFUXCQJVNQEBM-GBJGXRPFSA-M
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Compound Information
Molecular Weight:1035.1
Molecular Formula:C52H43Cl3O3Pd2
InChIKey:LNAMMBFJMYMQTO-FNEBRGMMSA-N
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Compound Information
Molecular Weight:232.1718
Molecular Formula:C12H9O3P
InChIKey:DLQYXUGCCKQSRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SECXISVLQFMRJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:480.2631
Molecular Formula:C16H17IN8O2
InChIKey:YJVJGMJRZVWJJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.98
Molecular Formula:C10H21NSn
InChIKey:WQHUTROLEJVBSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.3856
Molecular Formula:C17H20N8O2
InChIKey:QYSYOGCIDRANAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:423.4584
Molecular Formula:C24H25NO6
InChIKey:QAJLWVQSHLUJNO-MDGMKKHVSA-N
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Compound Information
Molecular Weight:286
Molecular Formula:C11H21NSn
InChIKey:QUGLKFNSYIUTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:375.4602
Molecular Formula:C24H25NO3
InChIKey:DJUVJYPORDYYLA-KVZQYWQLSA-N
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Compound Information
Molecular Weight:128.1723
Molecular Formula:C6H12N2O
InChIKey:GUVUOGQBMYCBQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.06
Molecular Formula:C15H23NSn
InChIKey:PKKUBJKHXAXDGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:425.5189
Molecular Formula:C28H27NO3
InChIKey:ZBBIQOUAMZWROC-FCSZGESBSA-N
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Compound Information
Molecular Weight:385.86
Molecular Formula:C9H18INSn
InChIKey:LBIPEELCAYDMHY-UHFFFAOYSA-M
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Compound Information
Molecular Weight:28.0532
Molecular Formula:C2H4
InChIKey:Not Available
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Compound Information
Molecular Weight:511.05
Molecular Formula:C24H54P2Pd
InChIKey:MXQOYLRVSVOCQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1488
Molecular Formula:C6H6
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JFNLZVQOOSMTJK-KNVOCYPGSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PSZPCAFRANQPLS-SOSBWXJGSA-N
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Compound Information
Molecular Weight:436.8
Molecular Formula:C13H29NSn2
InChIKey:RJPHXRWDAJULFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:834.65
Molecular Formula:C26H44FeI2P2Pd
InChIKey:JCJVDDAWLIRHDY-UHFFFAOYSA-L
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Compound Information
Molecular Weight:290.72
Molecular Formula:C3H9ISn
InChIKey:XGRPNCOKLIMKBN-UHFFFAOYSA-M
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