A Convenient Synthetic Method for Preparing 2, 5-Disubstituted 1, 6-Methano [10] annulenes from 1, 6-Diacetylcyclohepta-1, 3, 5-triene.

…, K Sano, R Miyatake, S Tomoda, C Hayakawa…

Index: Kuroda, Shigeyasu; Zuo, Shengli; Oda, Mitsunori; Fukuta, Atsushi; Kajioka, Takanori; Saito, Toyohiko; Furuta, Shinji; Tsukumo, Hitoshi; Sano, Kenji; Miyatake, Ryuta; Tomoda, Shozo; Hayakawa, Chiharu; Nozawa, Haruna Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 7 p. 1659 - 1671

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Citation Number: 8

Abstract

The reaction of 1, 6-diacetylcyclohepta-1, 3, 5-triene with various Grignard reagents gave high yields of addition products 5, which were treated with a catalytic amount of p- toluenesulfonic acid or pyridinium p-toluenesulfonate to afford 2, 5-disubstituted 2, 3-dihydro- 1, 6-methano [10] annulenes 6 via 1, 6-bis (1-substituted vinyl) cyclohepta-1, 3, 5-trienes 8 and 2, 5-disubstituted 3, 4-dihydro-1, 6-methano [10] annulenes 9. On the other hand, ...