Synthesis of 1,2,5,6-Tetrahydrophosphorin 1-Oxides and 1,2-Dihydrophosphorin 1-Oxides from 2,5-Dihydro-1H-phosphole 1-Oxide-Dichlorocarbene Adducts

Article abstract of DOI:10.1021/jo00235a014

Reaction of 6,6-dichloro-1-methyl-3-phosphinbicyclo<3.1.0>hexane 1-oxides 1 with silver nitrate in alkohols or water leads to the regioisomers of alkoxy- or hydroxy-1,2,3,6,tetrahydrophosphorin 1-oxides 2A and 2B or 3A and 3B.Each isomer consists of diastereoisomers.Water elimination from the hydroxy derivatives 3 results in the formation of the regioisomers of 1,2-dihydrophosphorin 1-oxides 4A and 4B.Constitution and strereostructure of the compounds has been elucidated by 1H, 13C, and 31P NMR spectroscopy.