Bedi Vaibhav, Mandal Dipendu, Hussain Zahid, Chen Shi-Ming, Wu Yile, Qu Zheng-Wang, Grimme Stefan, Stephan Douglas W
Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada.
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, China.
Dalton Trans. 2024 Jan 2;53(2):439-443. doi: 10.1039/d3dt03506a.
Reactions of (BuOCN) 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 (BuOCN) with 9-BBN leads to a bicyclic heterocyclic product (BuOCO(BBN)CN)1. In contrast, the reactions of (BuOCN) with BF or [EtSi][B(CF)] lead to the isolation of [BuNHNHBu][BF] 2 and [BuN(H)NBu][B(CF)] 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.
