Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products

Kasturi, Tirumalai R and Betageri, Rajesekhar and Gonibella, Raju J and Reddy, Gowravaram M and Ramamoorthy, Sivaramakrishnan and Narayanan, Ramasubbu and Kailasam, Venkatesan (1984) Oxidation of bis(2-hydroxy-1-naphthyl)methane and similar bisnaphthols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Structure and synthesis of novel products. In: Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (10). pp. 2375-2382.

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Abstract

Oxidation of bis(2-hydroxy-1-naphthyl)methane with DDQ gave the novel dispiro compounds cis- and trans-I together with spiro compounds II (n = 1, 2). The structures of I were detected by spectral methods. Hydrogenation of I gave 1-(2-hydroxy-1-naphthyl)methyl-2-(2-hydroxy-1-naphthyloxy)naphthalene by $C-C$ bond cleavage. A number of analogs of I were prepared similarly. A reaction mechanism involving quinol ether intermediates is proposed.

Item Type:	Journal Article
Publication:	Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	12 May 2008
Last Modified:	19 Sep 2010 04:44
URI:	http://eprints.iisc.ac.in/id/eprint/13928

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