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Synthesis 2003(7): 1112-1116
DOI: 10.1055/s-2003-39178
DOI: 10.1055/s-2003-39178
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Sulfinyl- and Sulfonyl-Substituted 2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as Potential Photochromic Compounds
Further Information
Received
22 November 2002
Publication Date:
09 May 2003 (online)
Publication History
Publication Date:
09 May 2003 (online)

Abstract
Some novel 2-benzylbenzoxazoles and 2-benzylbenzothiazoles, substituted at the 2′ position by electron-withdrawing groups, were synthesized via the lithiation of the benzoxazole or benzothiazole ring. The expected reversible photoinduced proton-transfer reaction of such compounds was studied.
Key words
benzylation - heterocycles - metalations - sulfones - photochemistry
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