An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements

David C. Harrowven; Mubina Mohamed; Théo P. Gonçalves; Richard J. Whitby; David Bolien; Helen F. Sneddon

doi:10.1002/anie.201200281

An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements

David C. Harrowven^*, Mubina Mohamed, Théo P. Gonçalves, Richard J. Whitby, David Bolien, Helen F. Sneddon

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates (see scheme).

Original language	English (US)
Pages (from-to)	4405-4408
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	18
DOIs	https://doi.org/10.1002/anie.201200281
State	Published - Apr 27 2012

Keywords

cyclobutenones
density functional calculations
photochemistry
rearrangements
small ring systems

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201200281

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title = "An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements",

abstract = "Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates (see scheme).",

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AU - Harrowven, David C.

AU - Mohamed, Mubina

AU - Gonçalves, Théo P.

AU - Whitby, Richard J.

AU - Bolien, David

AU - Sneddon, Helen F.

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AB - Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates (see scheme).

KW - cyclobutenones

KW - density functional calculations

KW - photochemistry

KW - rearrangements

KW - small ring systems

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ER -

An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements

Abstract

Keywords

ASJC Scopus subject areas

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