115579-08-3Relevant articles and documents
Reaction of Cyclic Phosphites with Haloacetones
Morita, Iwao,Tsuda, Masami,Kise, Masahiro,Sugiyama, Makoto
, p. 4711 - 4716 (2007/10/02)
Treatment of various cyclic phosphites (1), e.g.,2-methoxy-1,3,2-dioxaphosphorinane (1a), 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (1b) and 2-methoxy-1,3,2-dioxaphosphorane (1c), with haloacetones (2) gave cyclic Arbuzov products (3), cyclic Perkow products (4), cyclic methylphosphonates (5), and acyclic products (6-8).Compound 1a gave all of the products (3a,4a,5a,6ag,7ag,8ag).However, cyclic phosphites with substituents in the ring (1b,1d) gave only the cyclic products (3-5).The five -membered ring phosphite (1c) yielded only the acyclic products (6cg, 7cg).Treatment of 1a with chloroacetone gave only the Perkow products (4a,7ah).Cyclic phosphite (1f)with 2-benzyloxy substituenet afforded simply the cyclic products (3a, 4a, 9).A mechanistic interpretation of these reactions is presented. Keywords---cyclic phosphite; haloacetone; cyclic acetonylphosphonate; cyclic enol phosphate; Arbuzov reaction; Perkow reaction