Issue 11, 2000

Pyrolysis reactions of nonafluorobiphenyl-4-yl prop-2-enyl ether: a remarkable rearrangement reaction of an intramolecular Diels–Alder product

Abstract

The title compound 16 on flash vapour pyrolysis (FVP) at 350 °C gives a complex mixture which includes 20, the product of one of the two possible intramolecular Diels–Alder reactions of the cyclohexa-2,4-dienone intermediate 17 formed via a Claisen rearrangement reaction. FVP of 16 at 420 °C gives the bicyclic compound 30, formed not from the other possible Diels–Alder adduct 27 but from an isomer 31 having exactly the same carbon skeleton, but produced as a transient intermediate via a rare retro-cyclisation reaction of 20 to a tethered ketene 32 and recyclisation via the alternative mode.

Supplementary files

Article information

Article type
Paper
Submitted
18 Feb 2000
Accepted
24 Mar 2000
First published
09 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1731-1734

Pyrolysis reactions of nonafluorobiphenyl-4-yl prop-2-enyl ether: a remarkable rearrangement reaction of an intramolecular Diels–Alder product

A. S. Batsanov, G. M. Brooke, D. Holling and A. M. Kenwright, J. Chem. Soc., Perkin Trans. 1, 2000, 1731 DOI: 10.1039/B001356K

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