Unusual Rearrangements in Cage Compounds Due to Proximity Effects

Alfred Hassner*, Simha Naidorf-Meir, Hugo E. Gottlieb, Israel Goldberg

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The strained keto diol 5 underwent an unexpected rearrangement in the presence of H2O-TEA-CH3CN at 20 °C to afford two isomeric products 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.

Original languageEnglish
Pages (from-to)5699-5701
Number of pages3
JournalJournal of Organic Chemistry
Issue number21
StatePublished - 1993


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