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.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1915–1918, September, 2004.
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Shipov, A.E., Genkina, G.K., Petrovskii, P.V. et al. Arbuzov rearrangement in the 1,3,2-oxazaphosphinane series. Russ Chem Bull 53, 1996–1999 (2004). https://doi.org/10.1007/s11172-005-0061-6
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DOI: https://doi.org/10.1007/s11172-005-0061-6
Key words
- 2-alkoxy-1,3,2-oxazaphosphinanes
- 2-alkoxy-3-alkyl-1,3,2-oxazaphosphinanes
- Arbuzov rearrangement
- alkyl bromoacetates
- 2-alkoxycarbonylmethyl-2-oxo-1,3,2λ5-oxazaphosphinanes
- 2-alkoxycarbonylmethyl-3-alkyl-2-oxo- 1,3,2λ5-oxazaphosphinanes
- alkyl alkoxy[N-(3-bromopropyl) amino]phosphorylacetates
- alkyl alkoxy[N-alkyl-N-(3-bromopropyl)amino]phosphorylacetates
- cyclization