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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 4a 82 ± 2b 99 ± 1 93 ± 2
  1. Yields and conversion were measured by NMR
  2. aReaction was run 2 days at 50 °C, then 2 days at 60 °C
  3. bIsolated yield was 71 ± 2 %