The Journal of Organic Chemistry

Lewis acid-directed reactions of quinones with styrenyl systems: the case of 2-methoxy-3-methyl-1, 4-benzoquinone

TA Engler, R Iyengar

Index: Engler, Thomas A.; Iyengar, Rajesh Journal of Organic Chemistry, 1998 , vol. 63, # 6 p. 1929 - 1934

Full Text: HTML

Citation Number: 27

Abstract

Reactions of 2-methoxy-3-methyl-1, 4-benzoquinone with various (E)-1-propenylbenzenes promoted by 1 equiv of Ti (IV), as a 1: 1 mixture of TiCl4-Ti (Oi-Pr) 4, produce rel-(1 S, 6 R, 7 R, 8 R)-8-aryl-4, 7-dimethyl-3-methoxybicyclo [4.2. 0] oct-3-ene-2, 5-diones 3 and trans-2- aryl-3, 7-dimethyl-6-methoxy-2, 3-dihydro-5-benzofuranols 5 as the major products. Reactions promoted by 2 equiv of Ti (IV) as a 1: 1 mixture of TiCl4-Ti (Oi-Pr) 4 or 1 equiv of ...