Site Selectivity and Regioselectivity of the Hetero-Diels-Alder and Cheletropic Additions of Sulfur-Dioxide to a 2,3,6,7-Tetramethylidenebicyclo[3.2.1]Octane Derivative

At -55-degrees-C SO2 adds to 4-[(tert-butyl)dimethylsilyloxy]-1-methoxy-2,3,6,7-tetramethylidenebicyc lo[3.2.1]octane reversibly and selectively onto the s-cis-butadiene moiety at C(2), C(3) giving a single regioisomeric sultine. At -45-degrees-C the cheletropic addition of SO2 occurs selectively giving the monosulfolene attached at C(2), C(3).


Published in:
Tetrahedron Letters, 34, 39, 6269-6270
Year:
1993
ISSN:
0040-4039
Keywords:
Note:
Univ lausanne,chim sect,2 rue barre,ch-1005 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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