Remarkable enhancement of dienophilicity by the trifluoromethanesulfonyl group. Phenyl(trifluoromethanesulfonyl)acetylene

Richard S Glass, Douglas L. Smith

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

Phenyl(trifluoromethanesulfonyl)acetylene, 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
Volume39
Issue number25
StatePublished - 1974

Fingerprint

Acetylene
Cyclopentanes
Anhydrides
Lithium
Salts
Derivatives
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Remarkable enhancement of dienophilicity by the trifluoromethanesulfonyl group. Phenyl(trifluoromethanesulfonyl)acetylene. / Glass, Richard S; Smith, Douglas L.

In: Journal of Organic Chemistry, Vol. 39, No. 25, 1974, p. 3712-3715.

Research output: Contribution to journalArticle

@article{521c01348c1a4039a87762937ee341db,
title = "Remarkable enhancement of dienophilicity by the trifluoromethanesulfonyl group. Phenyl(trifluoromethanesulfonyl)acetylene",
abstract = "Phenyl(trifluoromethanesulfonyl)acetylene, 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.",
author = "Glass, {Richard S} and Smith, {Douglas L.}",
year = "1974",
language = "English (US)",
volume = "39",
pages = "3712--3715",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "25",

}

TY - JOUR

T1 - Remarkable enhancement of dienophilicity by the trifluoromethanesulfonyl group. Phenyl(trifluoromethanesulfonyl)acetylene

AU - Glass, Richard S

AU - Smith, Douglas L.

PY - 1974

Y1 - 1974

N2 - Phenyl(trifluoromethanesulfonyl)acetylene, 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)acetylene, 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.

UR - http://www.scopus.com/inward/record.url?scp=0000316881&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000316881&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0000316881

VL - 39

SP - 3712

EP - 3715

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 25

ER -