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Paper | Special issue | Vol 61, No. 1, 2003, pp.225-235
Published online, 4th August, 2003
DOI: 10.3987/COM-03-S22
The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

Yasuoki Murakami,* Akira Ishii, Hidehiko Ozawa, Hiroko Okahira, Keiko Hosokawa, Tomiko Tashiro, Jin-ichi Muto, Hideharu Suzuki, Masanobu Tani, and Yuusaku Yokoyama

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl-1,2,3,4-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.