A facile synthesis of [1‐13C]benzonitrile by bromination‐dehydrobromination of [1‐13C]1‐cyanocyclohexene
- 1 January 1983
- journal article
- research article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 20 (1) , 79-82
- https://doi.org/10.1002/jlcr.2580200111
Abstract
[1‐13C]1‐Cyanocyclohexene can be bisbrominated by N‐bromosuccinimide and then aromatized by triethylamine to give [1‐13C] benzonitrile in 90% yield. This allylic bisbromination‐dehydrobromination reaction is generally applicable to the transformation of other 1‐substituted cyclohexenes into benzenoid derivatives.Keywords
This publication has 7 references indexed in Scilit:
- Reorientation and transalkylation reactions of isotopically labeled toluene, ethylbenzene, and propylbenzeneThe Journal of Organic Chemistry, 1981
- Reactions of complex compounds of cobalt, part XI. Mechanism of the oxidative degradation of coordinated salicylateTransition Metal Chemistry, 1977
- 13C‐Angereicherte Monomere zur NMR‐Spektroskopie von PolymerenDie Angewandte Makromolekulare Chemie, 1976
- Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.Chemical Reviews, 1963
- Preparation of 1-13C Enriched Benzonitrile, Mono-13C Enriched Benzene, and a Mixture of Mono-13C Enriched Benzonitriles.Acta Chemica Scandinavica, 1962
- STRUCTURE AND PROPERTIES OF CYCLIC COMPOUNDS: XI. DISSOCIATION CONSTANTS OF THE CYANOHYDRINS OF SOME METHYLCYCLOHEXANONESCanadian Journal of Chemistry, 1958
- Syntheses of Benzene, Toluene and Benzoic Acid Labeled in the Ring with Isotopic CarbonJournal of the American Chemical Society, 1952