Journal
TETRAHEDRON
Volume 58, Issue 7, Pages 1301-1307Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)01224-8
Keywords
octatetraenes; allylic dienylic sulfones; Ramberg-Backlund reaction
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The reaction of allylic dienylic sulfone with dibromodifluoromethane in the presence of alumina-supported KOH in dichloro-methane solution results in facile rearrangement affording the corresponding all-trans 1,3,5,7-octatetraenes in excellent yields. This result shows that the double bonds of stereochemically defined allylic dienylic sulfone retain their stereochemistry and the newly formed double bond has an (E)-configuration in the modified Ramberg-Backlund procedure. (C) 2002 Elsevier Science Ltd. All rights reserved.
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