1,4 Addition of dicyanocarbene onto cyclooctatetraene

✍ Scribed by A.G. Anastassiou; R.P. Cellura; E. Ciganek

• Book ID: 104230082
• Publisher: Elsevier Science
• Year: 1970
• Tongue: French
• Weight: 179 KB
• Volume: 11
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99991-x

✦ Synopsis

CARBENES and nitrenes very rarely add to polyenes in a 1,4 fashion, only two such cases having been reported to date. 233 Presently, we briefly demonstrate that one of the primary products in the reaction of thermally generated (ca 80") dicyanocarbene with cyclooctatetraene (COT) is in fact a 1,4 adduct.

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The reaction under discussion was recently reported to furnish two products characterized as 1 (70%) and 2 (18$).6

Nevertheless, the less abundant component was assigned structure 2 only on a tentative basis and with considerable reservation since much of its chemistry was not deemed to be entirely as anticipated of a dihydroindene structure. It was noted6 for example, that the 5267