The Journal of Organic Chemistry

Formation of a novel norcamphor upon treatment of 2-hydroxy-4-isopentyl-4-methylcyclopentanone with acid

WC Agosta, S Wolff

Index: Agosta,W.C.; Wolff,S. Journal of Organic Chemistry, 1976 , vol. 41, # 15 p. 2605 - 2607

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Citation Number: 6

Abstract

Treatment of 2-hydroxy-4-isopentyI-4-methylcyclopentanone(1) with polyphosphoric acid or 85% phosphoric acidcan lead to 1-isopropyl-4-methylnorcamphor (2), as wellas the previouslyreported 1, 4, 4-trimethylbicyclo [3.2. 1]-octan-6-one (3). An alternative preparation of 2 from 4-methylnorcamphor (4) is described, and formation of 2 from 1 is rationalized in terms of intermediates 14-18. The series of rearrangements suggested includes a 1, 5- ...