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 β-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 and dichlorophosphonyl benzofulvene isomers. The generation process of acyl chloride-substituted chlorophosphonium ylide was carefully monitored by using P{H} NMR spectroscopy, and a plausible reaction mechanism was proposed.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.4c01720DOI Listing

Publication Analysis

Top Keywords

acyl chloride-substituted
16
chloride-substituted chlorophosphonium
16
reactions benzyl
8
benzyl phosphine
8
phosphine oxide/sulfide
8
chlorophosphonium ylides
8
chlorophosphonium ylide
8
oxide/sulfide cocl
4
cocl synthesis
4
synthesis novel
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!