Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

Mudududdla, Ramesh ; Sharma, Rohit ; Abbat, Sheenu ; Bharatam, Prasad V. ; Vishwakarma, Ram A. ; Bharate, Sandip B. (2014) Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes Chem. Commun., 50 (81). pp. 12076-12079. ISSN 1359-7345

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Official URL: http://doi.org/10.1039/C4CC05151C

Related URL: http://dx.doi.org/10.1039/C4CC05151C

Abstract

A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C–C bond cleavage followed by intermolecular [4+2]-Diels–Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:116431
Deposited On:12 Apr 2021 09:40
Last Modified:12 Apr 2021 09:40

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