Mechanism of the condensation-rearrangement reactions of tropone with 1,2-dimethoxybenzene under the action of concentrated sulfuric acid

doi:10.7523/j.issn.2095-6134.2016.01.010

Abstract

Abstract:

The reactions of tropone (cycloheptatrienone) gave the cycloaddition products frequently, and occasionally substitutions on the olefins bonds also occurred. For 1,2-dimethoxybenzene, previous studies concerned its condensation reactions with the different aldehydes or ketones,more limited to the aryl aldehydes or saturated aliphatic aldehydes and ketones, under the action of acid.We study the condensation reaction of conjugated polyene unsaturated ketone with o-dimethoxybenzene, and the results show that not only the dehydration condensation occurs under the action of acid, but also the interesting shrink ring rearrangement reaction occurs in which a seven-membered ring converts to a six-membered aromatic ring.

Key words: tropone, dimethoxybenzene, condensation reaction, rearrangement reaction, aromatization

CLC Number:

O621.3

ZHANG Tong, HE Wei, ZHU Zhongpeng, YANG Jingkui. Mechanism of the condensation-rearrangement reactions of tropone with 1,2-dimethoxybenzene under the action of concentrated sulfuric acid[J]. , 2016, 33(1): 65-69.

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