Variable mechanism of nucleophilic substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents. Issue 5 (24th December 2015)

• Record Type: Journal Article
• Authors: Yao, Lan; Liu, Li-Juan; Xu, Zhong-Yuan; Nie, Shao-Zhen; Xiao, Xiao-Qing; Zhao, Chang-Qiu
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 5(2016)
• Page Start: 1702
• Page End: 1706
• Publication Date: 2015-12-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01871d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The variable mechanism for substitution of P -stereogenic phosphoryl chloride with alkynyl metallic reagents depends on temperature, stoichiometry of starting materials, and the structure of the nucleophilic reagent. Abstract : The variable mechanism for substitution of P -stereogenic phosphoryl chloride with alkynyl metallic reagents, which depends on temperature, stoichiometry of starting materials, and the structure of the nucleophilic reagent, is assumed as either SN 2-like or Berry pseudorotation of pentacoordinated phosphorus intermediates, affording inversion and retention products, respectively. The formation of the inversion product can be controlled to occur predominantly to afford ( R P )-alkynylphosphinates.