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

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

Volume: 10 Issue: 1

Author(s): Stefan Jankowski and Krzysztof Huben

Affiliation:

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

Abstract: 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.

Cite this article as:

Jankowski Stefan and Huben Krzysztof, 2-Phospha- and 2,3-Oxaphosphabicyclo[2.2.2]octenes - Synthesis and Fragmentation to Low-coordinated Species, Current Organic Chemistry 2006; 10 (1) . https://dx.doi.org/10.2174/138527206775192988