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Synlett 1993; 1993(10): 781-783
DOI: 10.1055/s-1993-22607
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Cyanohydrins from Squaric Acid Ester with Trimethylsilyl Cyanide and Their Ring Opening Reactions

Yoshihiko Yamamoto* , Keiko Nunokawa, Masatomi Ohno, Shoji Eguchi
  • *Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
19 March 2002 (online)

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Cyanohydrin of squaric acid diester was obtained by addition of TMSCN catalyzed with ZnI2. Also direct O-ethyl cyanohydrin synthesis was performed by addition of the same reagent combined with Et3OBF4.13 These cyanohydrins were converted to 4 cyano-3-butenoate and -2-butenolide. The present method provides a new pave for the ring transformation of cyclobutenones.