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The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems

The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems
The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems
Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused ?-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50 °C to 180 °C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings
cyclobutenes, electrocyclic reactions, fused-ring systems, photochemistry, ring opening
1433-7851
1527-1531
Ralph, Michael J.
2b7d046b-a733-49ec-8289-aaea512c92fe
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Gaulier, Steven
bac76834-6e13-49a5-b5fb-f33b5c3ade00
Ng, Sean
9471eb01-1823-467e-b55a-b29301eabd83
Booker-Milburn, Kevin I.
422de450-72a6-4727-9d02-3b2b30a09777
Ralph, Michael J.
2b7d046b-a733-49ec-8289-aaea512c92fe
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Gaulier, Steven
bac76834-6e13-49a5-b5fb-f33b5c3ade00
Ng, Sean
9471eb01-1823-467e-b55a-b29301eabd83
Booker-Milburn, Kevin I.
422de450-72a6-4727-9d02-3b2b30a09777

Ralph, Michael J., Harrowven, David C., Gaulier, Steven, Ng, Sean and Booker-Milburn, Kevin I. (2015) The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems. Angewandte Chemie International Edition, 54 (5), 1527-1531. (doi:10.1002/anie.201410115).

Record type: Article

Abstract

Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused ?-lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50 °C to 180 °C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium-sized rings

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More information

Accepted/In Press date: 13 November 2014
e-pub ahead of print date: 5 December 2014
Published date: 26 January 2015
Keywords: cyclobutenes, electrocyclic reactions, fused-ring systems, photochemistry, ring opening
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 389692
URI: https://eprints.soton.ac.uk/id/eprint/389692
ISSN: 1433-7851
PURE UUID: 7e1f63c3-48e3-46c0-95e7-bc0378f5aea2
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Mar 2016 10:16
Last modified: 20 Jul 2019 01:19

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