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Updated: Jul 8, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
The impact of Lewis acid variation on reactions with di-tert-butyl diazo diesters
Vaibhav Bedi1, Dipendu Mandal1,2, Zahid Hussain2
1Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.
Abstract:
Reactions of (tBuO2CN)2 with Lewis acids and FLPs have previously been shown to prompt the formation of diazene compounds. In this work, we show that the reaction of (tBuO2CN)2 with 9-BBN leads to a bicyclic heterocyclic product (tBuOCO(BBN)CN)21. In contrast, the reactions of (tBuO2CN)2 with BF3 or [Et3Si][B(C6F5)4] lead to the isolation of [tBuNHNH2tBu][BF4] 2 and [tBuN(H)NtBu][B(C6F5)4] 3, respectively. The mechanism for the formation of 2 is probed computationally, demonstrating that steric and electronic considerations of the Lewis acid impact the reaction pathway.
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