Synlett p. 675 - 676 (1997)
Update date:2022-08-04
Topics:
Egusa, Kenji
Fukase, Koichi
Kusumoto, Shoichi
The 4-azido-3-chlorobenzyl (Cl-Azb) group was readily introduced to hydroxy functions by the use of a crystalline reagent, 4-azido-3-chlorobenzyl bromide, which was prepared from commercially available 2-chloro-4-methylaniline in two steps. Cl-Azb ethers have improved acid stability as compared to the corresponding parent 4-azidobenzyl (Azb) ether. Cl-Azb ethers were stable to direct 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) oxidation, but were cleaved smoothly by DDQ oxidation after conversion to the corresponding iminophosphorane derivative.
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Doi:10.1021/jo01258a016
(1969)Doi:10.1016/S0960-894X(97)00330-2
(1997)Doi:10.1007/BF00959961
()Doi:10.1055/s-1997-5756
(1997)Doi:10.1016/S0040-4039(97)00237-2
(1997)Doi:10.1016/0040-4020(68)88166-9
(1968)
