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Arbuzov rearrangement in the 1,3,2-oxazaphosphinane series
Authors:A E Shipov  G K Genkina  P V Petrovskii  T A Mastryukova
Institution:(1) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation
Abstract:Reactions of 2-alkoxy-1,3,2-oxazaphosphinanes (including 3-alkyl derivatives) with methyl and ethyl bromoacetates give two types of Arbuzov rearrangement products (cyclic and acyclic ones). The ratio between their yields is virtually independent of the nature of the substituent in position 3 of the starting reagent, being mainly determined by the nature of the substituent in the phosphorus bound alkoxy group and varying from 96 : 4 to 2 : 98. Acyclic products can be converted into cyclic ones.Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1915–1918, September, 2004.
Keywords:2-alkoxy-1  3  2-oxazaphosphinanes  2-alkoxy-3-alkyl-1  3  2-oxazaphosphinanes  Arbuzov rearrangement  alkyl bromoacetates  2-alkoxycarbonylmethyl-2-oxo-1  3  2lambda5-oxazaphosphinanes" target="_blank">gif" alt="lambda" align="BASELINE" BORDER="0">5-oxazaphosphinanes  2-alkoxycarbonylmethyl-3-alkyl-2-oxo- 1  3  2lambda5-oxazaphosphinanes" target="_blank">gif" alt="lambda" align="BASELINE" BORDER="0">5-oxazaphosphinanes  alkyl alkoxy[N-(3-bromopropyl) amino]phosphorylacetates  alkyl alkoxy[N-alkyl-N-(3-bromopropyl)amino]phosphorylacetates  cyclization
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