Silicon and tin-directed Tiffeneau-Demjanov reaction.
Silicon and tin substituents surprisingly have only a moderate directing effect on the Tiffeneau-Demjanov reaction. The low selectivity is rationalised as being due to the reactive nature of the diazonium ion leaving group, the weaker oxydiazene leaving group was found to give better yields of the silicon-directed ring expanded product.
School of Chemistry, The University of Melbourne, Parkville 3010, Melbourne, Australia.
Leonie
L
Chow
Melanie
M
McClure
Jonathan
J
White