The 2-bromo-1-chloroalkanal p-tosylhydrazones 11a and b react with triethylamine as base to give the azoalkenes 12, of which (1-chloro-2-phenylethenyl)tosyldiazene (12b) is obtained as a crystalline material at room temperature. 12b reacts with SbCl5 at -30 and -70 deg C to form different diazonium salts, which are treated with nucleophiles such as methanol and water.The products obtained (Schemes 3 and 4) indicate the formation of the phenylethenyldiazonium salt 20, which is stable up to -20 deg C. 20 adds nucleophiles like methanol or water as well as anisole at the CC triple bond before releasing nitrogen.
Helwig, Reinhard,Hanack, Michael
p. 1008 - 1021
(2007/10/02)
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