Silyl effects on 1,3-diphosphacyclobutane-2,4-diyl: ring-opening of tetrahydrofuran and promotion of reductive P-C cleavage

Shigekazu Ito; Trang Thi Thu Ngo; Koichi Mikami

doi:10.1002/asia.201300564

Silyl effects on 1,3-diphosphacyclobutane-2,4-diyl: ring-opening of tetrahydrofuran and promotion of reductive P-C cleavage

Chem Asian J. 2013 Sep;8(9):1976-80. doi: 10.1002/asia.201300564. Epub 2013 Jun 7.

Authors

Shigekazu Ito¹, Trang Thi Thu Ngo, Koichi Mikami

Affiliation

¹ Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552, Japan. ito.s.ao@m.titech.ac.jp

PMID: 23749413
DOI: 10.1002/asia.201300564

Abstract

Mind your "P"s: Silylated P-heterocyclic biradicals activated tetrahydrofuran to give the corresponding 4-siloxybutyl-substituted 1,3-diphosphacyclobutane-2,4-diyls via ring-opening of the solvent molecule. Reductive P-C bond cleavage was found as an alternative approach to 1,3-diphosphacyclobuten-4-yl anion. Redox properties of the new P-heterocyclic biradicals were discussed in terms of hitherto unknown substituent effects.

Keywords: bond cleavage; heterocycles; radicals; redox chemistry; ring-opening reactions.