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Structure and photochemistry of four adamantylacetophenones

TitleStructure and photochemistry of four adamantylacetophenones
Publication TypeJournal Article
Year of Publication1998
AuthorsFu, TY, Scheffer, JR, Trotter, J, Yang, J
JournalActa Crystallographica Section C-Crystal Structure Communications
Volume54
Pagination491-496
Date PublishedApr
Type of ArticleArticle
ISBN Number0108-2701
Keywords2 POLYMORPHS, ALPHA-ADAMANTYLACETOPHENONE, CRYSTAL-STRUCTURES
Abstract

The photochemistry and crystal structures of four alpha-adamantylacetophenones have been studied, namely, 1-(4-fluorophenyl)-2-(tricyclo[3.3.1.1(3,7)]dec-1-yl)ethanone [(1a), C18H21FO], 1-(4-cyanophenyl)-2-(tricyclo[3.3.1.1(3,7)]dec-1-yl)ethanone [(1b), C19H21NO], 1-(4-cyanophenyl)-2-(3-methyltricyclo[3.3.1.1(3,7)]dec-1-yl)ethanone [(1c), C20H23NO] and 1-(4-carboxyphenyl)2-(3-methyltricyclo[3.3.1.1(3,7)] dec-1-yl)ethanone [(1d), C20H24O3]. All four molecules adopt fairly similar conformations, with short gamma H...O contacts permitting hydrogen abstraction in the photochemical reactions. However, three of the compounds, (1a), (1b) and (1d), are photostable in the solid state and possible reasons for this unreactivity are considered.

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