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Sulfonation of norbornene with sulfur trioxide

✍ Scribed by B. H. Bakker; R. M. Schonk; H. Cerfontain

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
180 KB
Volume
109
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Sulfonation of norbornene 1 with the SO~3~‐dioxane complex affords the β‐sultone 2, which rearranges at room temperature to the γ‐sultone 3. Reaction of 1 with 2 equiv of SO~3~‐nitromethane yields the carbyl sulfate 4. Carbocations are not involved in the formation of either the β‐sultone or the carbyl sulfate.

πŸ“œ SIMILAR VOLUMES

Sulfonation of alkenes with sulfur triox
Sulfonation of alkenes with sulfur trioxide; stereospecific Ξ²-sultone formation
✍ Bert H Bakker; Hans Cerfontain πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 266 KB

Sulfonation of I-octene, (E)-I-deuterio-1-octene, and (Z)-and (El-4-octene with one mol-equiv of sulfur trToxide yields the B-sultones Ta-d respectively. The reaction proceeds stereospecifically via a concerted ci&&addition.

Reactions of alkenoic acids with sulfur
Reactions of alkenoic acids with sulfur trioxide; sulfonation and sulfo-lactonization
✍ Ruud M. Schonk; B. H. Bakker; H. Cerfontain πŸ“‚ Article πŸ“… 2010 πŸ› Elsevier Science 🌐 English βš– 882 KB

## Abstract The reactions of the alkenoic acid derivatives 1a–19a with sulfur trioxide were studied in the temperature range βˆ’60 to 25Β°C using dichloromethane as solvent and 1.5 equiv. of dioxane as reactivity moderator. The alkenoic acids 13a and 14a, having a ‐(CH~2~)~4~‐ and ‐(CH~2~)~7~‐ linkage