123500-80-1Relevant articles and documents
Study on the reactivity of the alkyne component in ruthenium-catalyzed [2 + 2] cycloadditions between an alkene and an alkyne
Jordan, Robert W.,Villeneuve, Karine,Tam, William
, p. 5830 - 5833 (2006)
The ruthenium-catalyzed [2 + 2] cycloadditions of norbornadiene with a variety of alkynes have been investigated. Electronic effect of the alkyne component has shown to play an important role on the rate of the cycloaddition, and the reactivity of the alkyne component increases dramatically as the alkyne becomes more electron deficient. Increase in the steric bulk of the alkyne component decreases the reactivity of the alkyne component. It was also found that chelation effect of propargylic alcohols greatly enhanced the reactivity of the alkyne component in the ruthenium-catalyzed [2 + 2] cycloadditions.
(Z)-AND (E)-1-CHLORO-1,2-BIS(PHENYLSULPHONYL)ETHYLENES: SYNTHONS OF BIS(PHENYLSULPHONYL)ACETYLENE AND OF TERMINAL ACETYLENES IN CYCLOADDITION REACTIONS
Cossu, Sergio,Lucchi, Ottorino De
, p. 569 - 576 (2007/10/02)
The cycloaddition reaction of both isomeric 1-chloro-1,2-bis(phenylsulphonyl)ethylenes 1 leads to the expected Diels-Alder adducts with a number of dienes.The (Z)-isomer is more reactive, but the adducts are dehydrochlorinated with more difficulty and in lower yields than the adducts derived from the cycloaddition of the (E)-isomer.The dehydrochlorinated products are bis(phenylsulphonyl)alkenes which formally derive from the cycloaddition of the hitherto unknown bis(phenylsulphonyl)acetylene.These compounds undergo addition-elimination reaction with Grignard reagents; the products, desulphonylated by sodium amalgam, can be considered as the Diels-Alder adducts of terminal acetylenes.
