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

TitleThe crystal structure of a simple enol formed in a single-crystal-to-single-crystal enolene rearrangement
Publication TypeJournal Article
Year of Publication2004
AuthorsChong, KCW, Patrick, BO, Scheffer, JR
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume82
Pagination301-305
Date PublishedFeb
Type of ArticleArticle
ISBN Number0008-4042
Keywordsenol, enolene, HYDROGEN-ATOM ABSTRACTION, PHOTODIMERIZATION, REARRANGEMENT, single crystal, STATE, thermal
Abstract

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.

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