Treatment of Dimethoxyparacyclophanes with Ammonium Cerium (IV) Nitrate.

M Takeshita, H Tsuzuki, M Tashiro

Index: Takeshita, Michinori; Tsuzuki, Hirohisa; Tashiro, Masashi Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 8 p. 2076 - 2082

Full Text: HTML

Citation Number: 4

Abstract

The treatment of dimethoxy [n] paracyclophanes (n= 7–12)(5),[2] paracyclo [2] thiophenophane (13), and dimethoxy [2.2] paracyclophane (8) with CAN in MeCN–water afforded 2, 4-cyclohexadien-1-ones 9,[8] paracyclophanedione 10, the ring-opened esters 11, and ketones 12. When the n value of 5 was 7, 8, or 9, rearrangement of the methylene bridge occurred and 9 was obtained as the main products. With the n value of 12, quinone ...