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Enamine Chemistry—XI:The reaction of enamines with styrene oxide

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
24
Issue
9
Identifiers
DOI: 10.1016/s0040-4020(01)91999-4

Abstract

Abstract Reaction of cylic enamines with styrene oxide has been shown to give cyclic O,N-ketals having a furan nucleus. Dilute acidic hydrolysis of 2-phenyl-8-(N-pyrrolidino)perhydrobenzofuran, V, prepared from 1-pyrrolidino-1-cyclohexene, gave 2-(2-hydroxy-2-phenylethyl)cyclohexanone, VIII. Treatment of V with oxalic acid gave 2-phenyl-2,3,4,5,6,7-hexahydrobenzofuran, VI, which by acidic hydrolysis produced VIII, and by aromatization with sulphur was converted to 2-phenylbenzofuran. Mechanistic considerations for this new reaction are presented.

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