V. N. Telvekar, B. S. Takale / Tetrahedron Letters 51 (2010) 3940–3943
3943
6. Representative procedure for the cleavage of 1,2-diaminobenzene (Table 1, entry
1): NaIO4 (1.98 g, 9.25 mmol) in H2O (10 mL) was stirred at room temperature
for 2 min, then 1,2-diaminobenzene (0.5 g, 4.62 mmol) was added to the stirred
solution. After completion of the reaction (TLC), the aqueous phase was
extracted with CHCl3 (3 Â 10 mL). The combined organic layers were washed
with dilute HCl (20 mL), followed by water (3 Â 20 mL), finally dried over
Na2SO4 and concentrated in vacuum. The remaining residue was purified by
column chromatography on silica gel (hexane/ethyl acetate = 9:1) to yield
mucononitrile (470 mg, 98%) as a colorless solid. Mp: 127 °C (lit.3a 128 °C); IR
(KBr, cmÀ1): 3019, 2220, 1622, 1551, 756; 1H NMR (300 MHz, CDCl3): 5.62–
5.65 (d, J = 10.2 Hz, 2H), 7.34–7.37 (d, J = 10.2 Hz, 2H); 13C NMR (75 MHz,
CDCl3): 106.15, 114.57, 142.65; MS (m/z) calcd for C6H4N: 104.109; found 104
(M+).
reaction time. Both these applications are general, practical, eco-
nomical, and efficient.
Acknowledgements
V.N.T. thanks All India Council for Technical Education (AICTE)
for financial support under Research Promotion Scheme (RPS)
and B.S.T. thanks C.S.I.R (New Delhi) for providing fellowship.
References and notes
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