5-Azahexenoyl radicals cyclize via nucleophilic addition to the acyl carbon rather than 5-exo homolytic addition at the imine
- 18 September 2002
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 20,p. 2338-2339
- https://doi.org/10.1039/b207729a
Abstract
Molecular orbital calculations predict that the 5-azahexenoyl radical ring closes via nucleophilic addition to the acyl carbon to afford the 5-exo product; CCSD(T)/cc-pVDZ//BHLYP/cc-pVDZ calculations predict energy barriers of 36.1 and 46.9 kJ mol−1 for the exo and endo cyclization modes of the 5-azahexenoyl radical, respectively.This publication has 1 reference indexed in Scilit:
- Synthesis of heterocycles by radical cyclisationJournal of the Chemical Society, Perkin Transactions 1, 2001