Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Synthesis and Substitution Reactions of N-Protected 2-(Phenylselenonylmethyl)pyrrolidines

Matthew A. Cooper and A . David Ward

Australian Journal of Chemistry 50(3) 181 - 188
Published: 1997


Alkyl phenyl selenides derived from the benzeneselenenyl chloride induced cyclization of N-protected pent-4-enylamines can be converted in good yield into the corresponding 2-hydroxymethyl- or 2- alkoxymethyl-substituted pyrrolidines by oxidation to the corresponding selenone, followed by reaction with water (or hydroxide) or with the corresponding alcohol. Details of the reactions and possible mechanisms for the substitution are discussed.

© CSIRO 1997

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