Stereochemical Assignment of (E)-and (Z)-2-(l-Naphthyl)-l-phenylpropene and Their Photocyclization to 5-Methylchrysene

Clinton E. Browne, Thomas K. Dobbs, Stephen S. Hecht, Edmund J. Eisenbraun

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Dehydration of 2-(l-naphthyl)-l-phenyl-2-propanol (3) gave varying ratios of (E)-2-(l-naphthyl)-l-phenyl-propene (4), (Z)-2-(l-naphthyl)-l-phenylpropene (5), and 2-(l-naphthyl)-3-phenylpropene (6), depending upon conditions and choice of reagent. Assignment of configuration to these alkenes by UV and 1H NMR spectroscopy was equivocal, but unambiguous assignment was made through comparison of chemical shifts in the NMR spectra of the cis diols and the corresponding cyclic phenylboronates prepared from 4 and 5. Photocyclization of 4 or 5 gave 5-methylchrysene (1), whereas 6 was inert.

Original languageEnglish (US)
Pages (from-to)1656-1660
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number9
DOIs
StatePublished - Jan 1 1978

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