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Communication | Special issue | Vol 56, No. 1-2, 2002, pp.113-117
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)60
Rearrangement Reaction of 2-Methyltetrahydropyrans Having a C1’-Mesyloxy Group on the C2-Side Chain with Zinc Acetate: Ring Expansion and Ring Opening Reactions

Yasuharu Sakamoto, Mina Koshizuka, Hiroyuki Koshino, and Tadashi Nakata*

*RIKEN(The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan


Rearrangements of four possible stereoisomers of 6-tert-butyl-2-(1’-mesyloxy)ethyl-2-methyltetrahydropyran with Zn(OAc)2 in aq. AcOH were investigated. Rearrangement-ring expansion and/or rearrangement-ring opening reactions took place depending on the stereostructure of the substrates.