Syntheesis and stereochemistry of acidolysis of some cyclohept-2-enylstannames and -silanes

Kitching W., Penman K.G., Laycock B. and Maynard I. (1988) Syntheesis and stereochemistry of acidolysis of some cyclohept-2-enylstannames and -silanes. Tetrahedron, 44 13: 3819-3831. doi:10.1016/S0040-4020(01)86639-4


Author Kitching W.
Penman K.G.
Laycock B.
Maynard I.
Title Syntheesis and stereochemistry of acidolysis of some cyclohept-2-enylstannames and -silanes
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
Publication date 1988-01-01
Sub-type Article (original research)
DOI 10.1016/S0040-4020(01)86639-4
Volume 44
Issue 13
Start page 3819
End page 3831
Total pages 13
Subject 1303 Specialist Studies in Education
1605 Policy and Administration
3002 Drug Discovery
Abstract A range of methyl-substituted cyclohept-2-enyltrimethylstannanes and trimethylsilanes have been synthesised and characterised by 1H, 13C and 119Sn (or 29Si) nmr spectroscopy. Key conformational characteristics of some of these compounds are discussed. Acidolysis of these stannanes and silanes (with CF3COOD) proceeds cleanly to provide the 2H-subatituted methylcycloheptene resulting from allylic rearrangement i.e. regiospecific γ-attack by the electrophile (SE'). Detailed examination of the 2H nmr spectra of the methylcycaloheptenes establishes a highly preferred, if not specific, γ-anti mode of electrophile delivery. Thus, this γ-anti-SE' process may form the basis of synthetically useful applications in what is sometimes an awkward ring system for functionalisation.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Citation counts: TR Web of Science Citation Count  Cited 16 times in Thomson Reuters Web of Science Article | Citations
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Created: Fri, 11 Mar 2016, 20:24:39 EST by Anthony Yeates