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Solid‐Acid Catalysed Rearrangement of Cyclic α,β‐Epoxy Ketones
Author(s) -
Elings Jacob A.,
Lempers Hans E. B.,
Sheldon Roger A.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1905::aid-ejoc1905>3.0.co;2-o
Subject(s) - chemistry , epoxy , ketone , carroll rearrangement , organic chemistry , acid catalysis , sigmatropic reaction , stereochemistry , medicinal chemistry , catalysis
Various cyclic α,β‐epoxy ketones rearranged to α‐formyl ketones and/or vic ‐diones in the presence of catalytic amounts of zeolites and montmorillonite K10. This provides an excellent alternative to conventional homogeneous systems with respect to yields and workup. Differences in product distribution and type of products in the rearrangement of pulegone oxide could be reasonably explained by invoking different pathways for homogeneous and heterogeneous catalysts.