Bicyclo[1.1.1]pentanone. Synthesis, Thermal Chemistry, and Photochemistry

Michael B. Sponsler, Dennis A. Dougherty

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Bicycle[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
DOIs
StatePublished - May 1984
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Bicyclo[1.1.1]pentanone. Synthesis, Thermal Chemistry, and Photochemistry'. Together they form a unique fingerprint.

  • Cite this