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Competition between cyclization, cleavage, and reverse hydrogen transfer in 1,4-hydroxybiradicals: Crystal structure-solid state reactivity correlations

TitleCompetition between cyclization, cleavage, and reverse hydrogen transfer in 1,4-hydroxybiradicals: Crystal structure-solid state reactivity correlations
Publication TypeJournal Article
Year of Publication2000
AuthorsCheung, E, Netherton, MR, Scheffer, JR, Trotter, J
JournalOrganic Letters
Volume2
Pagination77-80
Date PublishedJan
Type of ArticleArticle
ISBN Number1523-7060
KeywordsII REACTION, TETRAMETHYLENE
Abstract

[GRAPHICS] To provide experimental evidence on the relationship between stucture and reactivity in 1,4-hydroxybiradical intermediates, the Norrish type II photochemistry of a homologous series of spirobenzoyladamantane derivatives was investigated in the crystalline state and the outcome correlated with the structures of the compounds as determined by X-ray crystallography. The results provide an unusually detailed and compelling picture of the geometric factors responsible for the partitioning of these reactive intermediates among cleavage, cyclization, and reverse hydrogen transfer.

URL<Go to ISI>://000085554500021