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Synlett 1998; 1998(7): 757-760
DOI: 10.1055/s-1998-1777
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Benzyl Trityl Ether and DDQ as New Tritylating Reagents

Masato Oikawa* , Hiroaki Yoshizaki, Shoichi Kusumoto
  • *Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan; Fax 81-6-8 50-54 19; E-mail: skus@chem.sci.osaka-u.ac.jp
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Publication Date:
31 December 2000 (online)

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We describe herein a new tritylation procedure of alcohols using benzyl trityl ether and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The reaction involves oxidative abstraction of one of the benzylic protons of benzyl trityl ether, followed by transformation of the generated benzyl trityl ether cation into a complex of benzaldehyde and trityl cation. The present procedure proceeds under mild neutral conditions to afford trityl ethers in generally good yields for primary alcohols, and in acceptable yields for several secondary alcohols.

tritylation - benzyl trityl ether - DDQ