MOLECULAR STRUCTURE AND PHOTODECARBONYLATION OF 2,3,4,5‐ TETRAPHENYLCYCLOPENTANONE

Frederick D. Lewis*, Theodore L. Field, Michal Sabat

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Clemmensen reduction of tetracyclone yields r‐2,t‐3,t‐4,c‐5‐tetraphenylcyclopentanone, the structure of which was established by x‐ray crystallography. Photodecarbonylation of this molecule results in the formation of cis‐ and trans‐stilbenes and minor amounts of tetraphenykyclobutane. The stilbenes are initially formed in comparable yield, but secondary photoisomerization results in cw‐rich mixtures. Stepwise photodecarbonylation is proposed to yield triplet meso‐ 1,2,3,4‐tetraphenylbutane‐diyl which undergoes nonstereoselective elimination in preference to cyclization. The intermediacyof the same biradical in the photodimerization stilbene can be effectively eliminated on the basis of stereochemical evidence.

Original languageEnglish (US)
Pages (from-to)277-281
Number of pages5
JournalPhotochemistry and Photobiology
Volume52
Issue number2
DOIs
StatePublished - Aug 1990

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry

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