The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52) | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8309136

Reference Type

Journal Article

Title

The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

Author(s)

Murakami, Y; Ishii, A; Ozawa, H; Okahira, H; Hosokawa, K; Tashiro, T; Muto, JinI; Suzuki, H; Tani, M; Yokoyama, Y; ,

Year

2003

Is Peer Reviewed?

Yes

Journal

Heterocycles
ISSN: 0385-5414

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Page Numbers

225

DOI

10.3987/COM-03-S22

Web of Science Id

WOS:000188053700032

URL

http://www.heterocycles.jp/newlibrary/libraries/abst/01312
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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.