Phosphinidene group transfer to olefins is an ideal route to three-membered rings containing phosphorus, phosphiranes, themselves versatile building blocks in organophosphorus chemistry. To be described is a catalytic version of this reaction, with a simple iron organometallic complex as the catalyst, or pre-catalyst. Styrenes undergo the phosphiranation reaction in good yield, and the resulting phosphiranes are stable enough to be purified by distillation. Keeping in mind the notion of a phosphinidenoid key intermediate, with a role analogous to that of a carbenoid in cyclopropanation, we designed a route to tri-tert-butyl phosphatetrahedrane. The strain of this molecule will be put into a context of the full series of mixed phosphorus-carbon tetrahedranes. Some of its ring-opening and ensuing cycloaddition reactions will be described. All of the described chemistry benefits from the use of anthracene as a benign, neutral leaving group.

Strained molecules containing phosphorus

ACS Fall 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.