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2004
Rearrangements
O 0140
[2,3] Sigmatropic Rearrangement of Unstable Sulfur Ylides from Allyl Sulfonium
Comparative Study of Electrochemical Reduction with the Base Method
52- 035 Salts.
and Mechanism Elucidation by the MO Method. — The electrochemical reduction
of sulfonium salts (I) and (III) without benzaldehyde (V) yields the same [2,3] sigmatropic rearrangement products (II) as those obtained by treatment with a base. Reduction of sulfonium salts (I) in the presence of benzaldehyde (V) affords epoxides (VI) as
a result of a Corey-Chaykovsky reaction confirming ylide formation. — (OKAZAKI,
Y.; ANDO, F.; KOKETSU*, J.; Bull. Chem. Soc. Jpn. 77 (2004) 9, 1687-1695; Dep.
Appl. Chem., Coll. Eng., Chubu Univ., Aichi 487, Japan; Eng.) — M. Paetzel
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