Sustainable Chemical Processes

Table 3 Synthesis of compound 3 through [2 + 3] cycloaddition of p-toluenesulfonyl cyanide (3) and benzyl azide (1)

From: Butadiene sulfone as ‘volatile’, recyclable dipolar, aprotic solvent for conducting substitution and cycloaddition reactions

Entry	Solvent	Temp (°C)	Time (days)	Yield (%)	Conv. 1 (%)	Conv. 2 (%)
1	DMSO	50	4	30 ± 1	100 ± 0	47 ± 1
2	BS	70	1	70 ± 2	99.2 ± 0.1	89 ± 1
3	BS	50	1	50 ± 1	57 ± 2	51 ± 2
4	BS	50	4	77 ± 1	95 ± 1	91 ± 4
5	BS	50–60	4^a	82 ± 2^b	99 ± 1	93 ± 2

Yields and conversion were measured by NMR
^aReaction was run 2 days at 50 °C, then 2 days at 60 °C
^bIsolated yield was 71 ± 2 %

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