Investigations on Novel 1,3‐Diazetidine Based Four‐Membered N‐Heterocyclic Carbenes

Author:

Karl Leonard1ORCID,Meisner Jan2ORCID,Ganter Christian1ORCID

Affiliation:

1. Institute of Inorganic Chemistry and Structural Research Heinrich Heine University Düsseldorf Universitätsstraße 1 40225 Düsseldorf Germany

2. Institute for Physical Chemistry Heinrich Heine University Düsseldorf Universitätsstraße 1 40225 Düsseldorf Germany

Abstract

AbstractAttempts towards the synthesis of two novel four‐membered 1,3‐diazetidine based N‐heterocyclic carbenes (NHCs) containing an organic backbone with a carbonyl functionality were undertaken. These carbenes cannot be isolated but the respective carbene dimers are obtained in quantitative yield which undergo a degradation and rearrangement sequence upon thermal exposure. Some of the species involved in these thermal reactions could be isolated and characterized, others were observed by mass spectrometric experiments. Ab initio and density functional theory (DFT) calculations provide a mechanistic rationale for the experimental observations. Since dimerization is strongly favored, classic carbene trapping reactions remain a goal to achieve.

Publisher

Wiley

Subject

Inorganic Chemistry

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