Reactions of Benzyl Phosphine Oxide/Sulfide with (COCl)2: Synthesis of Novel Acyl Chloride-Substituted Chlorophosphonium Ylides

被引：0

作者：

Zhao, Peng ^{[1
]}

Liu, Mengting ^{[1
]}

Li, Ying ^{[1
]}

Wang, Lili ^{[1
]}

Duan, Zheng ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Int Phosphorus Lab, Zhengzhou 450001, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期

基金：

中国国家自然科学基金;

关键词：

OXALYL CHLORIDE; NUCLEOPHILIC-SUBSTITUTION; OXIDES; REDUCTION; PHOSPHONATES; CONVENIENT; ARYLATION; NITRILES; BORANES;

D O I：

10.1021/acs.joc.4c01720

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New reactions of benzyl phosphine oxide/sulfide with oxalyl chloride are presented. The resulting reactive intermediates, acyl chloride-substituted chlorophosphonium ylides, are capable of undergoing esterification and Friedel-Crafts acylation reactions, ultimately yielding either methyl 2-(2-bromophenyl)-2-(diphenylphosphoryl)acetate or beta-carbonyl-diarylphosphine oxide derivatives. Additionally, when an alkynyl group is contained in the acyl chloride-substituted chlorophosphonium ylide, intramolecular cyclization occurs, leading to the formation of a pair of trans- and cis-dichlorophosphonyl benzofulvene isomers. The generation process of acyl chloride-substituted chlorophosphonium ylide was carefully monitored by using P-31{H-1} NMR spectroscopy, and a plausible reaction mechanism was proposed.

引用

页码：14305 / 14314

页数：10