Bicyclo[1.1.1]pentanone. Synthesis, thermal chemistry, and photochemistry

Michael Sponsler, Dennis A. Dougherty

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Bicyclo[1.1.1]pentanone (1) has been prepared in two steps, the key reaction being the ozonolysis of 2-phenylbicyclo[1.1.1]pentan-2-ol (6). On heating, 1 undergoes cycloreversion to allylketene (13). The activation parameters and solvent effects for this process suggest that the reaction is concerted and that the transition state is relatively nonpolar. The predominant photochemical pathway for 1 is decarbonylation to bicyclobutane (16). Cycloreversion to 13 is a minor reaction mode. Both the thermal and photochemical results are rationalized by considering the high strain energy and novel geometrical features of 1, and, in the latter case, the unusually high energy of its 1(nπ*) state.

Original languageEnglish (US)
Pages (from-to)4978-4984
Number of pages7
JournalJournal of Organic Chemistry
Volume49
Issue number25
StatePublished - 1984
Externally publishedYes

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Pentanones
Photochemical reactions
Strain energy
Chemical activation
Heating
Hot Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bicyclo[1.1.1]pentanone. Synthesis, thermal chemistry, and photochemistry. / Sponsler, Michael; Dougherty, Dennis A.

In: Journal of Organic Chemistry, Vol. 49, No. 25, 1984, p. 4978-4984.

Research output: Contribution to journalArticle

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