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Table 2 Nucleophillic substitution reaction of benzyl halides with inorganic azide salts in sulfolenes and DMSO

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

Entry Solvent Reactants Reaction time (h) Yielda (%)
1 DMSO [8] BnBr, NaAz 1 98
2 PS BnCl, NaAz 3 6 ± 0
3 BS BnCl, NaAz 1
3
49 ± 5
86 ± 4
4 BS BnCl, 1.5 NaAz 1
3
65 ± 2
93 ± 1
5 DMSO (1 % H2O)b BnCl, NaAz 1 97 ± 0
6 BS (1 % H2O) BnCl, NaAz 1
3
93 ± 1
95 ± 1
7 BS (1 % H2O) BnCl, CsAz 1 96 ± 0
8 BS BnBr, NaAz 1 100c
  1. aGC yield
  2. b1 % water by volume
  3. cNMR yield, BnBr (2.5 M)