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Synlett 1997; 1997(6): 675-676
DOI: 10.1055/s-1997-3258
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4-Azido-3-chlorobenzyl Ether, New Protection for Hydroxy Functions

Kenji Egusa, Koichi Fukase1 , Shoichi Kusumoto2
  • 1Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560, Japan, Fax 06 850 5419; Internet koici@chem.sci.osaka-u.ac.jp
  • 2Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560, Japan, Fax 06 850 5419
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Publication History

Publication Date:
31 December 2000 (online)

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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.

p-azidobenzyl type - improved acid-stability - oxidative cleavage - selective deprotection

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