Issue 18, 2016
From the journal:

Organic & Biomolecular Chemistry

Synthetic transformation of 1,3-diarylisobenzofuran-DMAD adducts: a facile preparation of tri-substituted α-naphthols†

Jayachandran Karunakaran,a   Meganathan Nandakumar,a   Natarajan Senthil Kumara  and  Arasambattu K. Mohanakrishnan*a  

* Corresponding authors

a Department of Organic Chemistry, School of Chemical Sciences University of Madras, Guindy Campus, Chennai - 600 025, Tamil Nadu, India
E-mail: mohanakrishnan@unom.ac.in, mohan_67@hotmail.com

Abstract

1,3-Diarylisobenzofuran-DMAD adducts upon reaction with BF3·OEt2 in DCM at room temperature underwent a regiospecific 1,2-aryl migration followed by the Krapcho decarboxylation to give tri-substituted α-naphthols in good yields.

Graphical abstract: Synthetic transformation of 1,3-diarylisobenzofuran-DMAD adducts: a facile preparation of tri-substituted α-naphthols

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Article information

DOI
https://doi.org/10.1039/C6OB00628K
Article type
Paper
Submitted
23 Mar 2016
Accepted
05 Apr 2016
First published
05 Apr 2016

Org. Biomol. Chem., 2016,14, 4247-4259

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Synthetic transformation of 1,3-diarylisobenzofuran-DMAD adducts: a facile preparation of tri-substituted α-naphthols

J. Karunakaran, M. Nandakumar, N. Senthil Kumar and A. K. Mohanakrishnan, Org. Biomol. Chem., 2016, 14, 4247 DOI: 10.1039/C6OB00628K

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