Abstract
The strained keto diol 5 underwent an unexpected rearrangement in the presence of H 2 O-TEA-CH 3 CN at 20 o C to afford two isomeric product 6 and 7. The latter two compounds undergo further conversion to carboxy keto diol 8. The structures of 6-8 were elucidated by heterero COSY experiments and in the case of 6 by X-ray diffraction. The transformation of 5 to 6 and 7 is interpreted as involving an unusual retroaddition of a benzylic anion to a cyclobutanone 5→10. This is facilitated by subsequent readdition of this anion to another proximally located ketone with formation of a cyclopropanol 11, which is immediately converted to 6 and 7
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