Selenoxides, 0-oxidoalkyl

Further reaction of Aese species with carbonyl compounds and hydrolysis of the resulting alkoxide leads to p-oxidoalkyl selenoxides which have been transformed into allyl alcohols on thermal decomposition (Schemes 51, 52 and 54, entry a see Section 2.6.4.4) or reduced to p-hydroxyalkyl selenides or to alkenes (Scheme 53). P-Oxidoalkyl selenoxides derived from cyclobutanones react in a different way since Aey rearrange to cyclopentanones upon heating (Scheme 54, b. Schemes 120 and 121 and Section 2.6.4.5.3). 

Strained -oxidoalkyl i enyl selenoxides, such as l-oxido-l-(r-phenylsdenoxyalkyl)cyclopropanes, derived from oxaspiropentanes with tetraalkyl-substituted oxirane rings, and l-(r-hydroxyalkyl)-l-selenoxycyclobutanes, - obtained on oxidation of the corresponding selenides or on reaction of a-li-thioalkyl selenoxides with cyclobutenones, possess a high propensity to rearrange to cyclobutanones... 

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