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Butadiene sulfone has been employed as a “volatile”, recyclable dipolar, aprotic solvent in the reaction of benzyl halide with metal azides to form benzyl azide (1) and the subsequent reaction of benzyl azide with p-toluenesulfonyl cyanide (3) to produce 1-benzyl-5-(p-toluenesulfonyl)tetrazole (2). Comparisons are made with the solvent DMSO and an analogous sulfolene solvent—piperylene sulfone. In addition, recycling protocols for butadiene sulfone and piperylene sulfone are also presented.
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Huang et al. (2015) studied this question.
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