Chemical and Photochemical Behavior of Nondissociating Cyclopentadienone Dimers

Benzion Fuchs*, Mordechai Pasternak, Barak Pazhenchevsky

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The nondissociating character and endo configuration of the substituted cyclopentadienone dimers 2c,d along with the novel “mixed dimers” 2e,f were unequivocally demonstrated. Irradiation of the dimers 2c,d brings about only reversible 1,3-rearrangement to 11c,d of all the possible modes available to the system (Scheme IV). In contrast to that, the “mixed dimers” 2e,f undergo only internal cycloaddition to the dissymmetric cage products 6e,f. Stereoelectronic arguments are put forward to rationalize this behavior in a general framework of this class of compounds.

Original languageEnglish
Pages (from-to)2017-2020
Number of pages4
JournalJournal of Organic Chemistry
Issue number10
StatePublished - May 1981


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