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Diels–Alder and Ene Reactions of the Stannaethene Me 2 Sn=C(SiMe 3 ) 2 : Dienophilic and Enophilic Behaviour of Ethenes Me 2 E=C(SiMe 3 ) 2 (E=Si, Ge, Sn)
Author(s) -
Wiberg Nils,
Wagner Susanne,
Vasisht ShamKumar
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19981204)4:12<2571::aid-chem2571>3.0.co;2-4
Subject(s) - ene reaction , steric effects , chemistry , cycloaddition , medicinal chemistry , stereochemistry , carbon fibers , catalysis , order (exchange) , organic chemistry , mathematics , composite number , finance , algorithm , economics
An analogy to carbon has been established for the reported unsaturated compounds Me 2 Sn=C(SiMe 3 ) 2 , Me 2 Ge=C(SiMe 3 ) 2 and Me 2 Si=C(SiMe 3 ) 2 in the study of their dieno‐ and enophilicity. The Diels–Alder and ene reactions of Me 2 E=(SiMe 3 ) 2 (E = Sn, Ge or Si) with butadienes and propenes take place both regioselectively and stereoselectively and are governed by electronic and steric effects. The trend towards ene reaction decreases at the cost of [4+2] cycloaddition in the order sila‐, stanna‐, germaethene.