Cyclobutenyl derivatives of phosphorus and sulfur

Abstract

Diethylphosphine and methanethiol react with the cyclobutenes [Formula: see text](X = Cl, F) to give the compounds (C2H5)2 [Formula: see text] (Y = Cl, F) and [Formula: see text] (Y = F, Cl, C2H5). The disubstituted compound [Formula: see text] is also obtained from CH3SH and [Formula: see text].The related di(tertiary phosphine) (C6H5)2- [Formula: see text] can similarly be prepared. Methanethiol adds to [Formula: see text] to give the cyclobutane, but reacts with [Formula: see text]to give [Formula: see text]and with [Formula: see text] to give the cyclobutenone [Formula: see text]. Tetra-methyldiphosphine and [Formula: see text] yield the disubstituted compound [Formula: see text], whereas a cyclobutenone is obtained when (C6H5)2P—P(C6H5)2 reacts with [Formula: see text]. In some reactions, the phosphorane (C6H5)2PF3 is obtained, probably from (C6H5)2PF.