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

Richard S. Glass; Douglas L. Smith

doi:10.1021/jo00939a023

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

Richard S. Glass, Douglas L. Smith

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50 Scopus citations

Abstract

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 language	English (US)
Pages (from-to)	3712-3715
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	39
Issue number	25
DOIs	https://doi.org/10.1021/jo00939a023
State	Published - Dec 1 1974
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Remarkable Enhancement of Dienophilicity by the Trifluoromethanesulfonyl Group. Phenyl(trifluoromethanesulfonyl)acetylene",

abstract = "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.",

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T1 - Remarkable Enhancement of Dienophilicity by the Trifluoromethanesulfonyl Group. Phenyl(trifluoromethanesulfonyl)acetylene

AU - Glass, Richard S.

AU - Smith, Douglas L.

PY - 1974/12/1

Y1 - 1974/12/1

N2 - 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.

AB - 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.

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

Abstract

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