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The Nazarov Reaction of 1-Acryloyl-1,3,5-cycloheptatriene; a Novel Synthetic Pathway from 1,3,5-Cycloheptatriene to Dihydro-1(2H)-azulenone

✍ Scribed by Oda, Mitsunori ;Yamazaki, Takafumi ;Kajioka, Takanori ;Miyatake, Ryuta ;Kuroda, Shigeyasu

Book ID: 102366895
Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 382 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719971221

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✦ Synopsis

Abstract

The title compound, 1‐acryloyl‐1,3,5‐cycloheptatriene (3), was prepared from 1,3,5‐cycloheptatriene in four steps, and subsequently its Nazarov cyclization of 3 was studied in order to develop a novel synthetic pathway to dihydro‐1(2__H__)‐azulenone. While the reaction of 3 in sulfuric acid afforded 1‐tetralone (5) in a low yield, the reaction in a mixture of phosphoric acid and formic acid at room temp. produced 3,8‐dihydro‐1(2__H__)‐azulenone (6) and 3,3a‐dihydro‐1(2__H__)‐azulenone (7) in yields of 46 and 13% respectively. Using stannic chloride as the acid in the reaction gave 6 and 7 in a slightly better combined yield.

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