Halogenated Epoxides. 61. Reactions of Selected Chlorooxiranes with Sodium Methoxide: About the Question of Acetylenic and Allenic Epoxides as Intermediates

Article abstract of DOI:10.1021/jo00178a021

Reactions of sodium methoxide with five chlorooxiranes (1, 3, 11, 18, and 19) and with the corresponding isomeric chlorocarbonyl compounds have been examined.In two cases the chlorooxirane and the corresponding chlorocarbonyl compound afforded the same products, however, in different yields.In the other cases the chlorooxiranes and the corresponding chlorocarbonyl compounds gave different products.It is concluded that chlorocarbonyl compounds are not formed to a large extent as intermediates.In the reactions of two chlorooxiranes (18 and 19) with sodium methoxide, acetylenic and allenic epoxides may be invoked as transient intermediates.