81362-47-2Relevant academic research and scientific papers
The mild preparation of synthetically useful phosphonic dichlorides: Application to the synthesis of cyclic phosphonic diesters and diamides
Stowel,Ueland,McClard
, p. 3261 - 3262 (2007/10/02)
A very mild method for the preparation of synthetically useful phosphonic dichlorides has been developed and its application toward the synthesis of 2-alkyl-2-oxo-1,3,2-dioxophosphorinanes and 1,3-dimethyl-2-alkyl-2-oxo-1,3,2-diazaphospholidines is reported.
PHOTOREARRANGEMENTS OF BENZYL PHOSPHITES. STEREOCHEMISTRY AT PHOSPHORUS
Cairns, Matthew S.,Bentrude, Wesley G.
, p. 1025 - 1028 (2007/10/02)
The photo-Arbuzov rearrangement of a cyclic benzyl phosphite is shown to proceed with retention of configuration at phosphorus.The mechanistic and potential synthetic implications of this result are discussed.
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
