1990•SynlettRequires access

Single and Double Nucleophilic Addition to Coordinated Pi-Hydrocarbons: Manganese-Mediated Functionalization of Arenes

Robert D. Pike, Dwight A. Sweigart

Abstract

All articles of this category A range of carbon-donor nucleophiles add to the arene ring in (arene)Mn(CO) 2 L + cations to give neutral cyclohexadienyl complexes that liberate monofunctionalized arenes upon oxidative removal of the metal. Treatment of the cyclohexadienyl complexes with the nitrosonium salt NOPF 6 affords cationic metal nitrosyl complexes that are attacked by a second nucleophile to give cis - and trans -difunctionalized 1,3-cyclohexadienes. When the metal center is chiral, this procedure provides a route to enantiomerically pure cyclohexadienes. 1. Introduction 2. Mechanism of Nucleophilic Addition 3. Single Nucleophilic Addition 4. Double Nucleophilic Addition 5. Conclusions

About this research paper

What this paper is about

Why it matters

OpenAlex reports 72 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

Key concepts: Chemistry, Nucleophile, Cationic polymerization, Nucleophilic addition, Medicinal chemistry, Manganese, Ring (chemistry), Oxidative addition