Volume 20, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Stable Carbocations. Part 274. 2-Seco(1.1.1.1)pagodyl Cation. Strong Stabilization of a Trivalent Carbocation by C-C σ-Bond Hyperconjugation.

G. K. S. PRAKASH

G. K. S. PRAKASH

Inst. Org. Chem. Biochem., Univ. Freiburg/Br., D-7800 Freiburg/Br.

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W.-D. FESSNER

W.-D. FESSNER

Inst. Org. Chem. Biochem., Univ. Freiburg/Br., D-7800 Freiburg/Br.

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G. A. OLAH

G. A. OLAH

Inst. Org. Chem. Biochem., Univ. Freiburg/Br., D-7800 Freiburg/Br.

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G. LUTZ

G. LUTZ

Inst. Org. Chem. Biochem., Univ. Freiburg/Br., D-7800 Freiburg/Br.

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H. PRINZBACH

H. PRINZBACH

Inst. Org. Chem. Biochem., Univ. Freiburg/Br., D-7800 Freiburg/Br.

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First published: May 2, 1989

Abstract

Whereas all attempts to monoprotonate the pagodane (I) only give the known dication (II); the desired monocation (IV) is obtained either from the valence isomer (III), from chloride (Va) or from seco-pagodane (Vb).

ChemInform Abstract

Whereas all attempts to monoprotonate the pagodane (I) only give the known dication (II); the desired monocation (IV) is obtained either from the valence isomer (III), from chloride (Va) or from seco-pagodane (Vb). In superacid solution, monocation (IV) is quite stable even at 0 °C and is quenched by MeOH (VI) to give (Vc).

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