NOVEL FRAGMENTATION OF SPIRO CAGE DIONES DURING CE(IV) ION OXIDATION - INTERESTING MECHANISTIC DEVIATION THROUGH SPIRO ANNULATION

Oxidation of pentacyclo[5.4.0.0(2,6)0(3,1)0(5,9)]undecane-8,11-dione-4-spiro-1'-cyclopropane (2a) and pentacyclo[5.4.0.0(2,6)0(3,10).0(5,9)]undecane-8,11-dione-4-spiro-1'-cyclopentane (2b) with Ce (IV) ion is described. The treatment of 2a and 2b with ceric ammonium nitrate (CAN) furnishes...

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Published inIndian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry Vol. 31; no. 11; pp. 725 - 728
Main Authors SINGH, RAJU, BNS
Format Journal Article
LanguageEnglish
Published NEW DELHI Natl Inst Science Communication & Information Resources-Niscair 01.11.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OLEFIN METATHESIS
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Summary:Oxidation of pentacyclo[5.4.0.0(2,6)0(3,1)0(5,9)]undecane-8,11-dione-4-spiro-1'-cyclopropane (2a) and pentacyclo[5.4.0.0(2,6)0(3,10).0(5,9)]undecane-8,11-dione-4-spiro-1'-cyclopentane (2b) with Ce (IV) ion is described. The treatment of 2a and 2b with ceric ammonium nitrate (CAN) furnishes the isomeric anhydrides 3a, 4a and 3b, 4b and the ketolactones 5a, 5b, respectively. A mechanism has been proposed to account for the observed products.
ISSN:0376-4699
0019-5103