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Oxiranylidene intermediate in the reaction of trans-2-chloro-3- tert-butyloxirane with sodium phenoxide.

โœ Scribed by Harlan L. Goering; Steven D. Paisley

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
226 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The reaction of trans-2-chloro-3-(t-butyl)oxirane with sodium phenoxide in acetonitrile to give trans-2-phenoxy-3-(t-butyl)oxirane involves a-elimination to give an oxiranylidene which undergoes a stereoselective stepwise addition of phenol to give product.

Recently it was shown that reaction of trans-2-chloro-(l-Cl) or

2-bromo-3-(t-butyl)oxirane (1-Br) with phenoxides in acetonitrile results in replacement of halide by phenoxide with retention of configuration to give trans-2-phenoxy-3-(t-butyl)oxirane (2).l On the basis of kinetic studies,

๐Ÿ“œ SIMILAR VOLUMES

Nucleophilic substitution at a saturated
Nucleophilic substitution at a saturated carbon atom with retention of configuration: The reaction of trans-2-halo-3-tert-butyloxiranes with phenolates
โœ Johann Gasteiger; Karlheinz Kaufmann; Christian Herzig; T.William Bentley ๐Ÿ“‚ Article ๐Ÿ“… 1985 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 195 KB

Whereas reaction of trans-2-chloro or 2-bromo-3-tert-butyloxirane with thiophenc Zate occuรฏ>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