✍ Scribed by Schmittel, Michael ;Kiau, Susanne
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Four novel aryl‐substituted enediynes 3 have been synthesized. While their cyclization to the Bergman products 4 could be accomplished at temperatures of 240–320°C, α‐functionalization rather than cyclization was observed during anodic oxidation and in the presence of one‐electron oxidants. In contrast, enediyne 1a was cyclized in the presence of two one‐electron oxidants to the indenone 2a as indicated in the literature; mechanistic investigations clearly indicate the occurrence of an acid‐catalyzed mechanism.
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## Abstract The thermal cyclization of the phosphane oxide substituted enyne‐allene 1d results in the formation of 4d, an unknown double‐bond shift isomer of the 11__H__‐benzo[__b__]fluorene system. Because of the completely hindered rotation about the PC bond, two rotamers could be isolated and i
Thermal and Electron Transfer Induced Reactions of Enediynes and Enyne-Allenes. Part 14. Cyclization of Carbonyl Substituted Enyne-Allenes: C 2 -C 6 -Cyclization Induced by Heat or by Addition of Samarium(II) Iodide, Samarium(III) Chloride, or Boron Trifluoride. -The title enyne-allenes (VIII) and (