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Addition of Free Me 2 Ge: to Alkenes and Alkynes on Glass Surfaces in the Presence of Water
Author(s) -
Neumann Wilhelm P.,
Sakurai Hideki,
Billeb Gilbert,
Brauer Hartmut,
Köcher Jürgen,
Viebahn Sabine
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198910281
Subject(s) - anhydrous , phenylacetylene , acrylonitrile , yield (engineering) , silica gel , chemistry , silica glass , organic chemistry , materials science , catalysis , polymer , composite material , copolymer
Traces of water on glass surfaces (even after heating) can decisively influence the course of a reaction. This is shown by the reactions of Me 2 Ge: with alkenes such as acrylonitrile and alkynes such as phenylacetylene in “anhydrous” medium. These reactions afforded poor yields of 1 and 2 , respectively. On the other hand, reaction in the presence of water and silica gel gave 1 and 2 in nearly quantitative yield; the presence of water alone did not increase the yield. These findings indicate that acidic H atoms, formed on the silica surface, are essential for the reaction of the expected products with water.