Volume 26, Issue 6
Natural Products
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ChemInform Abstract: Ring-Opening of (-)-Camphorsulfonimide Derivatives and (+)- Fenchonesulfonimide by Nitronium Tetrafluoroborate.

G. WAGNER

G. WAGNER

Inst. Org. Chem. Biochem., TU Muenchen, D-85747 Garching, Germany

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U. VERFUERTH

U. VERFUERTH

Inst. Org. Chem. Biochem., TU Muenchen, D-85747 Garching, Germany

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R. HERRMANN

R. HERRMANN

Inst. Org. Chem. Biochem., TU Muenchen, D-85747 Garching, Germany

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C. KRUEGER

C. KRUEGER

Inst. Org. Chem. Biochem., TU Muenchen, D-85747 Garching, Germany

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First published: February 7, 1995

Abstract

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ChemInform Abstract

In the course of the reaction the S-N bond is cleaved off and the S-F and N-N bonds are formed immediately. Since this mechanism requires a close neighbourhood of the NO+ 2 and BF- 4 ions the reaction only takes place at the surface of the NO2BF4 crystal. The endosubstituted camphor derivatives react in higher yields due to the preferred orientation of the NO+ 2 ion to the less hindered endo-halogen.

chemical structure image

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