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Synfacts 2007(10): 1113-1113  
DOI: 10.1055/s-2007-968960
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Self-Indicating Linker for the Solid-Phase Isothiocyanate Synthesis

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
B. A. Burkett*, J. M. Kane-Barber, R. J. O’Reilly, L. Shi
Victoria University of Wellington, New Zealand
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Various isothiocyanates were synthesized from aldehydes and polymer-supported thiobenzophenone. The polymer-supported thiobenzophenone 1 was prepared from the PS-DVB co-polymer in two steps (eq. 1). The 1,3-dipolar cycloaddition of the hydroximoyl chlorides, prepared from the corresponding aldehydes, with 1, was carried out in the presence of triethylamine in toluene at 0 °C to afford the polymer-supported oxathiazol 2 (eq. 2). Subsequent Lewis acid assisted fragmentation of the resulting polymer 2 gave the isothiocyanates 3 (60-84% yield).