The Journal of Organic Chemistry

Phosphonic acids and esters. XX. Preparation and ring opening reactions of. alpha.,. beta.-and. beta.,. gamma.-epoxyalkylphosphonates. The proton magnetic …

CE Griffin, SK Kundu

Index: Griffin,C.E.; Kundu,S.K. Journal of Organic Chemistry, 1969 , vol. 34, p. 1532 - 1539

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Citation Number: 60

Abstract

Diethyl (Sa) and dimethyl (3b) a,@-epoxyethylphosphonates have been prepared by the epoxidation of the corresponding vinylphosphonates with t-butyl hydroperoxide in the presence of a basic catalyst. These epoxides fail to undergo thermal or acid-catalyzed rearrangements in contrast to the behavior of their@-substituted analogs. Both 3 and diethyl@,-y-epoxypropylphosphonate (4) undergo conventional hydrations, alcoholyses, ...