The crystal structure of a simple enol formed in a single-crystal-to-single-crystal enolene rearrangement

When crystals of 9-tricyclo[4.4.1.0]undecalyl-4-(carbomethoxy)phenyl ketone ( 1 ) were allowed to stand in the dark for extended periods of time at room temperature, the compound underwent a thermal reaction — the enolene rearrangement — to afford enol 2 . The crystals remained transparent and appea...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 82; no. 2; pp. 301 - 305
Main Authors Chong, Kenneth CW, Patrick, Brian O, Scheffer, John R
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.02.2004
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HYDROGEN-ATOM ABSTRACTION
single crystal
thermal
enol
STATE
PHOTODIMERIZATION
rearrangement
enolene
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Summary:When crystals of 9-tricyclo[4.4.1.0]undecalyl-4-(carbomethoxy)phenyl ketone ( 1 ) were allowed to stand in the dark for extended periods of time at room temperature, the compound underwent a thermal reaction — the enolene rearrangement — to afford enol 2 . The crystals remained transparent and appeared unchanged in shape as the reaction proceeded. X-ray diffraction data were collected on single crystals containing 17%, 25%, 66%, and 100% of the enol. The crystal structure of a simple enol was obtained via this novel single-crystal-to-single-crystal enolene rearrangement.Key words: single crystal, thermal, rearrangement, enol, enolene.
ISSN:0008-4042
1480-3291
DOI:10.1139/v03-207