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Dichotomic Reactivity of a Stable Silylene toward Terminal Alkynes: Facile CH Bond Insertion versus Autocatalytic Formation of Silacycloprop‐3‐ene
Author(s) -
Yao Shenglai,
van Wüllen Christoph,
Sun XiaoYing,
Driess Matthias
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704939
Subject(s) - silylene , autocatalysis , adduct , chemistry , autocatalytic reaction , acetylene , terminal (telecommunication) , reactivity (psychology) , alkyne , ene reaction , stereochemistry , medicinal chemistry , computer science , catalysis , organic chemistry , physics , silicon , telecommunications , statistical physics , medicine , alternative medicine , pathology
Jekyll and Hyde : Stable silylene 1 reacts readily with acetylene at room temperature to give 1,1‐adduct 2 , whereas at −78 °C only silacycloprop‐3‐ene 3 is formed. Once 3 is present in the reaction mixture, it autocatalyzes its own generation even at room temperature. Both the facile silylene CH bond insertion for terminal alkynes and the autocatalytic formation of silacycloprop‐3‐enes are unprecedented. R=2,6‐ i Pr 2 C 6 H 3 .