Chemical and nuclear magnetic resonance studies of 3,3‐diphenyltetrahydrofuran derivatives

P. S. Portoghese, D. A. Williams

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Pyrolytic cyclization of a‐ and β‐methadol methiodides afforded cis and trans isomers of 2‐ethyl‐3,3‐diphenyl‐5‐methyltetrahydrofuran, respectively. Catalytic hydrogenation of 2‐ethyli‐dene‐3,3‐diphenyl‐5‐methyltetrahydrofuran yielded the cis and trans isomers in a 2:1 ratio. The nmr spectra of these and structurally related compounds have been analyzed in terms of a half‐chair conformation for 2‐ethyl‐5‐methyl, 2‐ethyl, and 5‐methyl derivatives. An envelope conformation has been suggested for the compounds containing a double bond at C‐2.

Original languageEnglish (US)
Pages (from-to)307-312
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume6
Issue number3
DOIs
StatePublished - Jun 1969

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