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All-cis cyclonona-1,3,5,7-tetraene. Synthesis; thermal and photochemical reorganization.

✍ Scribed by A.G. Anastassiou; V. Orfanos; J.H. Gebrian

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
173 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

Owing to our recent synthesis of N-carbethoxylazonin (1) and oxonin we became quite interested in the title compound (all-cis CNT) 1 as an ideal classical-polyenic model. Furthermore, our recent description of the various reorganization pathways availa.ble to both ground and excited state CNT, (3) coupled with subsequent experimental information concerning the possible intermediacy of this tetraene in the thermal rearrangement of various 9substituted bicyclo[6.l.O]nona-2,4,6-trienes, (&a-c) provided additional incentive for isolating 1. We presently report on the synthesis, isolation and bond reorganization of this coveted substance.

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## Abstract Condensation of 1,3,4‐trimethyl‐1,5‐dihydro‐2__H__‐pyrrol‐2‐one, prepared in high yield from 3,4‐dimethylpyrrole, with pyrrole‐2‐carboxaldehyde and 1‐methylpyrrole‐2‐carboxaldehyde gives a mixture of Z‐ and __E__‐1,3,4‐trimethyl‐2,2′‐pyrromethen‐5[1__H__]‐one (7 and 8) and 1,1′,3,4‐tetr