Tetracyanoethylene as an aromatizing agent

✍ Scribed by Daniel T. Longone; Gary L. Smith

• Book ID: 104212517
• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 134 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70859-8

✦ Synopsis

TCNE) has proven to be an extremely versatile chemical intermediate. 1 The reactions of TCNE with conjugated dienes have been well delineated. In contrast to normal Diels-Alder adductions 293 with conjugated acyclic and cisoid cyclic dienes, Spiro-compounds 4-6 are generated by cycloaddition of TCNE to the exocyclic double bond in transoid methylenecycloalkenes. Less commonly, the cycloaddition of TCNE to an endocyclic double bond can yield a bicyclohexane derivative. 5 Supplementing its reactions with conjugated dienes we wish to report that TCNE functions as an efficient hydrogen acceptor in the aromatization of certain non-conjugated cycloalkadienes. The facile addition' of TCNE to norbornadiene to give the homo-Diels-Alder adduct I led us to investigate the reactions of TCNE with other nonconjugated dienes. In an attempt7 to generate the tricylodctane derivative II, a solution containing equimolar amounts of 1,4-cyclohexadiene and TCNE 1 T.L. Cairns et al d J. Amer. Chem. Sot. a, 2775 (1958).