A straightforward,high yielding and stereoselective synthesis of 3,4-dihydro-4-aryloxy-3-bromo-2H-l-benzopyrans compounds 8 and 9 by Mitsunobu coupling of the corresponding bromohydrins is reported. © 1994, Taylor & Francis Group, LLC. All rights reserved.

Kalpathy Chidambareswaran Santhosh

Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

benzopyran derivative

ether derivative

ORGANOBROMINE DERIVATIVE

article

drug synthesis

infrared spectrophotometry

Mass spectrometry

nuclear magnetic resonance

reaction analysis

stereochemistry

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

A Facile and Stereoselective Synthesis of Arylethers of Vicinal Bromohydrins by Mitsunobu Reaction

Synthetic Communications

A systematic study of the behaviour of aryl γ-halopropargyl ethers under thermal condition was undertaken. Aryl γ-bromopropargyl ethers 2 underwent unique transformation in N,N-diethylanillne (215°C, 6 h) giving rise to a mixture of products 3,4and 5, whereas, under similar conditions aryl γ-chloropropargyl ethers ulbar|8, afforded 4-chlorochromenes, 9. A remarkable substituent and solvent effect has been observed in the thermolysis of these aryl γ-bromo and γ-chloropropargyl ethers, rendering this transformation as a method for the synthesis of a number of substit uted 4-bromochromenes 3, 4-chlorochromenes 9 and chroman-4-ones 7. In contrast, solution thermolysis of aryl γ-iodopropargyl ether 11 afforded aryl propargyl ether 1 as the major product. © 1989.

Tetrahedron

Thermal behaviour of aryl γ-haloprcpargyl ethers

Chemistry of Heterocyclic Compounds: A Series Of Monographs Chemistry of Heterocyclic Compounds

Alkoxychromans

Helvetica Chimica Acta

Mitteilungen

J. Chem. Soc., Chem. Commun.

σ-π Mixing in phenylpentamethyldisilane

Journal of the Chemical Society C: Organic

The stereochemistry and reactions of some 3,4-disubstituted chromans

A facile and stereoselective synthesis of arylethers of vicinal bromohydrins by mitsunobu reaction

Journal	Synthetic Communications
ISSN	00397911
Open Access	No