Thermally induced cyclobutenone rearrangements and domino reactions
Thermally induced cyclobutenone rearrangements and domino reactions
Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.
cyclization, domino reactions, rearrangement, spiro compounds, thermochemistry
catalyzed ene-reactions, o-quinone methides, regiospecific synthesis, furaquinocin-e, acid, 1, 4-benzoquinones, hydroxyquinones, construction, chemistry
425-428
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Pascoe, David D.
15deb860-264b-4bdd-8b73-10fddabdadeb
Guy, Ian L.
b7d1bed5-2418-43d4-bb05-1db8d1bcc2db
2007
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Pascoe, David D.
15deb860-264b-4bdd-8b73-10fddabdadeb
Guy, Ian L.
b7d1bed5-2418-43d4-bb05-1db8d1bcc2db
Harrowven, David C., Pascoe, David D. and Guy, Ian L.
(2007)
Thermally induced cyclobutenone rearrangements and domino reactions.
Angewandte Chemie International Edition, 46 (3), .
(doi:10.1002/anie.200603538).
(PMID:17146823)
Abstract
Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.
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Published date: 2007
Additional Information:
Communication
Keywords:
cyclization, domino reactions, rearrangement, spiro compounds, thermochemistry
catalyzed ene-reactions, o-quinone methides, regiospecific synthesis, furaquinocin-e, acid, 1, 4-benzoquinones, hydroxyquinones, construction, chemistry
Identifiers
Local EPrints ID: 44583
URI: http://eprints.soton.ac.uk/id/eprint/44583
ISSN: 1433-7851
PURE UUID: ce1dacbb-3b4d-4693-8349-b5125192cf0c
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Date deposited: 05 Mar 2007
Last modified: 16 Mar 2024 02:46
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Author:
David D. Pascoe
Author:
Ian L. Guy
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