Reactions of ethyl and tert-butyl phosphorodiamidites with chloroacetone, bromoacetone, and alpha-chloroethyl acetate were studied. The reaction pathway is determined by the structure of the intermediate quasiphosphonium compound responsible for the formation of the Arbuzov product as well as for the occurrence of the amonalous reaction yielding vinyl phosphate.
Reactions of tert-butyl tetraethylphosphorodiamidite with acetic and trifluoroacetic acids involve substitution of the amido group. Ibis process was described by a scheme beginning with protonation of phosphorus and proved by modeling separate reaction stages. A probable scheme of the proposed reactions is described.
Sal'keeva, L. K.; Usmanova, L. N.; Gazizov, T. Kh., Journal of general chemistry of the USSR, 1992, vol. 62, # 2.1, p. 269 - 273
作者:Sal'keeva, L. K.、Usmanova, L. N.、Gazizov, T. Kh.
DOI:——
日期:——
Gazizov, T. Kh.; Sal'keeva, L. K.; Gafurov, E. K., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 1028 - 1029
作者:Gazizov, T. Kh.、Sal'keeva, L. K.、Gafurov, E. K.、Kazantsev, A. V.
DOI:——
日期:——
——
作者:L. K. Sal'keeva、M. T. Nurmaganbetova、O. Sh. Kurmanaliev
DOI:10.1023/a:1025624116438
日期:——
The reactions of 2-tert-butoxy-3-phenyl-1,3,2-oxazaphospholane and di-tert-butyl diethylphosphoramidite with carbon tetrachloride and chloroform were studied. These reactions proceed via formation of an intermediate quasiphosphonium compound. In the process, carbon tetrachloride acts as a source of positively charged halogen, and chloroform, as a C-H acid.
Mechanism of Reactions of P(III) Amidoesters with Carboxylic Acid Chlorides
作者:L. K. Sal'keeva、M. T. Nurmagambetova、O. Sh. Kurmanaliev
DOI:10.1023/b:rugc.0000016008.08714.a5
日期:2003.9
——
作者:L. K. Sal'keeva、M. T. Nurmaganbetova、O. Sh. Kurmanaliev
DOI:10.1023/a:1013930431749
日期:——
Reactions of tert-butyl tetraethylphosphorodiamidite with benzylideneacetylacetone, benzylideneacetoacetic ester, and benzylidenemalonic ester are studied. It is shown that the reaction pathway significantly depends on the solvent and temperature. The reaction with benzylidenacetylacetone in ether gives rise to a stable diketophosphonate, while the same reaction in boiling benzene involves elimination of diethylamine and yields a phospholene. The reaction with benzylideneacetoacetic ester proceeds analogously, while with benzylidenemalonic ester the corresponding phospholene is formed exclusively.