✦ LIBER ✦

Research on photochemical and thermochemical reactions between indole and quinones in the absence of solvent

✍ Scribed by Yong-Mei Wang; Zhong Wen; Xiao-Min Chen; Da-Ming Du; Teruo Matsuura; Ji-Ben Meng

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 284 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350209

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✦ Synopsis

Abstract

The solid state photochemical reaction of indole with 1,4‐naphthoquinone yielded 5__H__‐dinaphtho[2,3‐a:‐2′,3′‐c]carbazole‐6,11,12,17‐tetrone (1) in addition to 2‐(3‐indolyl)‐1,4‐naphthoquinone (2) which was also the only product in the solution photoreaction. Solventless thermochemical reactions of indole with phenanthrenequinone in the presence or absence of zinc chloride gave 10‐(1__H__‐indol‐3‐yl)‐9‐phenanfhrenol (3) and 9,10‐dihydro‐9‐(1__H__‐indol‐3‐yl)‐10‐(3__H__‐indol‐3‐ylidene)‐9‐phenanthrenol (4) or 10,10‐di‐1__H__‐indol‐3‐yl‐9(10__H__)‐phenanthrenone (5), respectively. All of these products were only obtained in trace amount in corresponding solution reactions, and are different from the adduct 10‐hydroxy‐10‐(1__H__‐indol‐3‐yl)‐9(10__H__)‐phenanthrenone (6) obtained in the solution photoreaction. A possible mechanism for formation of 4 and 5 is described in terms of electron pair donor/acceptor complexation.

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