Tetrahedron p. 3819 - 3832 (1988)
Update date:2022-09-26
Topics:
Kitching, William
Penman, Kerry G.
Laycock, Bronwyn
Maynard, Ian
A range of methyl-substituted cyclohept-2-enyltrimethylstannanes and trimethylsilanes have been synthesized 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-substituted methylcycloheptene resulting from allylic rearrangement i.e. regiospecific γ-attack by the electrophile (SE').Detailedexamination of the 2H nmr spectra of the methylcycloheptenes establishes a highly preferred, if not specific, γ-anti mode of electrophile delivery.Thus, this γ-anti-SE' process may from the basis of synthetically useful applications in what is sometimes an awkward ring system for functionalization.
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