Benzaldehyde reacts with 2,4,4,5,5-pentamethyl-l,3,2-dioxaphospholane (1) to afford an oxaphosphirane (2) and its dimeric form dioxadiphosphorinane (3) in equilibrium.It is known that benzaldehyde reacts with tricovalent phosphorus derivatives leading to either a 2 : 1 adduct (Scheme 1)1,2 or a 1 : 1 adduct when it is stabilized as a zwitterionic species(I).3 With a-ethylenic ketones, ylides or phosphoranes were obtained4 (Scheme 2).We report here the reaction between benzaldehyde and 2,4,4,5,5-pentamethyl-l,3,2-dioxaphospholane (1) in dichloromethane at room temperature, resulting in a white solid after addition of hexane [m.p. 184°C (decomp.), 60%]. The remaining solution still contains a small amount of (4) and, when the solvent is not well degassed, the oxidation product of (1) (6 31P 40 p.p.m.). The elemental analyses of the new compound correspond to a 1 : 1 adduct.This compound could be oxaphosphirane (2a) or one of its zwitterionic forms (2b) (-'P+-C-Oor (2c) (:P+-0-C-.31P-{lH} n.m.r. spectra show a singlet near -25 p:p.m.,
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.