Rearrangement in the tricyclo[5.2.2.01,5]undecane series

Publication Type
Journal contribution
Authors
Spitzner, D.; Weber, W.; Kraus, W.
Year of publication
1982
Published in
Tetrahedron Lett.
Band/Volume
23/21
Page (from - to)
2179-82
Abstract

Treatment of the tricycloundecane I (R = CO2Me, R1 = H, R2 = OH) with 85% H2SO4 at room temp. gave 95% (crude yield) of a 2:1 mixt. of the rearranged lactones II together with a small amt. of olefin III (R = CO2Me, R1 = H). Similar treatment of I (R = H, R1 = CO2Me, R2 = .alpha.-OH) gave 90% (crude yield) of a 1:1 mixt. of III (R = H, R1 = CO2Me) and lactone IV. The reaction mechanisms are discussed.

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