Stereochemistry of Photocycloaddition of (E)-1,2-Dicyano- and (Z)-1,2-Diethoxyethylene to 5-Substituted Adamantanones

Wen-Sheng Chung, Nicholas J. Turro*, Sushil Srivastava, William J. le Noble

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


The photocycloaddition of olefins to 5-substituted adamantanones produces two geometrically isomeric oxetanes in which the oxygen atom and the 5-substituent are in anti or syn positions. The substituent was varied from fluoro, chloro, bromo, hydroxyl, and phenyl to tert-butyl. Although the mechanisms of the reaction with electron-rich and electron-poor olefins are quite different, the product ratios are similar (~60:40) in all instances. The preference of product formation from the attack on the zu face is discussed in terms of transition-state hyperconjugation.

Original languageEnglish
Pages (from-to)5020-5025
Number of pages6
JournalJournal of Organic Chemistry
Issue number17
StatePublished - 1 Aug 1991

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