Remarkable Enhancement of Dienophilicity by the Trifluoromethanesulfonyl Group. Phenyl(trifluoromethanesulfonyl)acetylene

Richard S. Glass, Douglas L. Smith

Research output: Contribution to journalArticlepeer-review

29 Scopus citations


Phenyl(trifluoromethanesulfonyl)acetyIene, prepared from the lithium salt of phenylacetylene and trifluoromethanesulfonic acid anhydride, undergoes exceptionally facile Diels-Alder reactions with tetraphenylcyclopentadienone, 1,3-diphenylisobenzofuran, cyclopentadiene, and 1,3-cyclohexadiene. The rates of these reactions and those of the corresponding reactions with other C6H5C≡CX derivatives were measured and compared. The rate of reaction of phenyl(trifluoromethanesulfonyl)acetylene with cyclopentadiene in ethyl acetate at room temperature was found to be 1.7 times as fast as the rate of reaction of dimethyl acetylenedicarboxylate with this diene. The reasons for the remarkable dienophilicity of phenyl(trifluoromethanesulfonyl)acetylene are discussed.

Original languageEnglish (US)
Pages (from-to)3712-3715
Number of pages4
JournalJournal of Organic Chemistry
Issue number25
StatePublished - Dec 1 1974

ASJC Scopus subject areas

  • Organic Chemistry


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