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The Mechanism of Addition of Phenols to Tetramesityldisilene. Evidence for Both
 

Summary: The Mechanism of Addition of Phenols to
Tetramesityldisilene. Evidence for Both
Nucleophilic and Electrophilic Rate-Determining
Steps
Yitzhak Apeloig* and Moshe Nakash
Department of Chemistry
Technion-Israel Institute of Technology
Haifa 32000, Israel
ReceiVed May 23, 1996
Following the synthesis of the first stable disilene, tetramesi-
tyldisilene (1), in 1981,1 many reactions of disilenes have been
chronicled.2 However, information about the mechanisms of
these reactions is still rather scarce. One of the most studied
mechanisms is that of the 1,2-addition reaction of alcohols to
the SidSi bond, but also this mechanism is not fully under-
stood.2 Addition of alcohols to (E)-1,2-di-tert-butyl-1,2-di-
mesityldisilene gives a 1:1 mixture of the two diastereoisomeric
alkoxysilanes, suggesting a stepwise mechanism involving a
zwitterionic intermediate.3 In contrast, theoretical calculations
(at the RHF/6-31G* level) predicted a four-center concerted

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry