2-Phospha- and 2,3-Oxaphosphabicyclo[2.2.2]octenes - Synthesis and Fragmentation to Low-coordinated Species

Author(s): Stefan Jankowski, Krzysztof Huben.

Journal Name: Current Organic Chemistry

Volume 10 , Issue 1 , 2006

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The 2-phosphabicyclo[2.2.2]octene and 2,3-oxaphosphabicyclo[2.2.2]octene systems undergo fragmentation in inert solvents on heating, or by UV-irradiation at room or low temperature. The fragmentation is of significance because it leads to the extrusion of low-coordinated species Y-P(X)O (Y = RO, R2N, Aryl; X = O, S, CH2), which are very effective phosphorylating agents. This review covers different aspects of the 2-phosphabicyclo[2.2.2]octene and 2,3-oxaphosphabicyclo[2.2.2]octene derivatives. The first part is focused on their synthesis and structure. The reactivity of 2,3-oxaphosphabicyclooctenes involving rearrangement and fragmentation with release of the bridging P-O unit including mechanistic studies is described in the next part. The last part of the review is dedicated to the practical aspects of the utilization these compounds as phosphorylating agents.

Keywords: N-phenylmaleimide, one-pot synthesis, O-insertion reaction, Dihydrophosphinine Oxides, Thermal fragmentation, metaphosphonate group

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Article Details

Year: 2006
Page: [79 - 92]
Pages: 14
DOI: 10.2174/138527206775192988

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