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Synthesis 1995; 1995(5): 571-576
DOI: 10.1055/s-1995-3944
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Triethyloxonium Tetrafluoroborate Mediated Addition Reaction of Unsaturated Organosilanes to Squaric Acid Esters

Yoshihiko Yamamoto, Keiko Nunokawa, Kohichi Okamoto, Masatomi Ohno, Shoji Eguchi*
  • *Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan, Fax +81(52)7893199
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Publication Date:
31 December 2000 (online)

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Squaric acid esters were treated with triethyloxonium tetrafluoroborate at room temperature to produce ethoxycarbenium ion species, and subsequent addition of trimethylsilyl cyanide (TMSCN) to this intermediate at 0°C afforded O-ethyl cyanohydrins in fair to good yields. In a similar manner, the ester reacted effectively with silyl enol ether and silyl ketene acetal to give the corresponding O-ethylated addition products. On the other hand the reaction with allylsilanes preferred the formation of 1:2 adducts.

squaric acid - unsaturated organosilane - Meerwein’s salt - 4-ethoxycyclobutenone