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Nucleophilic substitution at a saturated carbon atom with retention of configuration: The reaction of trans-2-halo-3-tert-butyloxiranes with phenolates

✍ Scribed by Johann Gasteiger; Karlheinz Kaufmann; Christian Herzig; T.William Bentley

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
195 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Whereas reaction of trans-2-chloro or 2-bromo-3-tert-butyloxirane with thiophenc Zate occuï>s at C-3 to gi7>e 2-phenylmercapto-3,3-dimethyZbutanaZ,phenoZates give substitution at C-2 witk retention of tke oxirane ring and retention of configuration witk kinetics tkat indicate a bimoZecuZar meckanism. Alkyl-substituted Z-chloro-and 2-bromooxiranes,I and 2_,l can be taken as model compounds for the study of the influente of electronic, steric, and strain energy effects on nucleophilic aliphatic substitution.2 Compounds I and 2 provide two sites for nucleophilic attack: carbon atom 2 has the lower electron density and therefore should be the favored site of attack.

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