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Gas‐Phase Synthesis of 1‐Silacyclopenta‐2,4‐diene
Author(s) -
Yang Tao,
Dangi Beni B.,
Thomas Aaron M.,
Sun BingJian,
Chou TzuJung,
Chang Agnes H. H.,
Kaiser Ralf I.
Publication year - 2016
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.201602064
Subject(s) - organosilicon , diene , gas phase , chemistry , molecule , phase (matter) , product (mathematics) , computational chemistry , combinatorial chemistry , organic chemistry , natural rubber , geometry , mathematics
Silole (1‐silacyclopenta‐2,4‐diene) was synthesized for the first time by the bimolecular reaction of the simplest silicon‐bearing radical, silylidyne (SiH), with 1,3‐butadiene (C 4 H 6 ) in the gas phase under single‐collision conditions. The absence of consecutive collisions of the primary reaction product prevents successive reactions of the silole by Diels–Alder dimerization, thus enabling the clean gas‐phase synthesis of this hitherto elusive cyclic species from acyclic precursors in a single‐collision event. Our method opens up a versatile and unconventional path to access a previously rather obscure class of organosilicon molecules (substituted siloles), which have been difficult to access through classical synthetic methods.