Synthesis of. alpha.-phosphono lactones and esters through a vinyl phosphate-phosphonate rearrangement

JA Jackson, GB Hammond…

Index: Jackson, John A.; Hammond, Gerald B.; Wiemer, David F. Journal of Organic Chemistry, 1989 , vol. 54, # 20 p. 4750 - 4754

Full Text: HTML

Citation Number: 42

Abstract

Upon treatment with base, the diethyl vinyl phosphate derivatives of five-, six-, and seven- membered-ring lactones undergo rearrangement to a-phosphono lactones in very good yields. Because the vinyl phosphates can be prepared in situ, these a-phosphono lactones can be obtained from the parent lactones in a one-flask protocol, making this methodology a convenient alternative to the traditional Arbuzov synthesis. An analogous reaction ...