Sulfonation of 1-butenes with sulfur trioxide

Abstract

15) MSH prepared by the exact procedure from ref 14 has exploded on several occasions in our laboratory. Our modified procedure results in small MSH crystals. To date we have not encountered difficulties in handling or storing (several months at 0°) MSH prepared by this modified method. R. Y. Ning, Chem. Eng. News, 36 (December 17, 1973), has recently issued a note of caution concerning MSH.

Analysis of SO3‐Sulfonation products of 1‐Alkenes by spectrometric methods

“…Attempts at preparing alkenesulfonic acids from 3-methyl 1-pentene, and 2,3,3-trimethyl 1 butene (16) were unsuccessful. It should be noticed that 3,3-dimethyl-1 butene gives, after rearrangement, the same acid as 2,3-dimethyl 1-butene (I; R, R2, R3 = CH3), whereas in the former case, only a 3"sultone was mentioned by Robbins (16). In addition, the main product of the sulfonation of 2,4,4-trimethyl 1-pentene seems to be the (Z)-isomer of the 2-alkene sulfonic acid, rather than the 1-alkenesulfonic acid proposed by Bordwell and Osborne (11).…”

“…Several publications (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) describe results on this subject. We report here the analytical part of a study concerning the SO3-sulfonation of some linear and branched 1alkenes (Cs to C14) in liquid phase according to the general scheme: In addition to chemical methods, e.g., degradative oxidation, the principal analytical techniques used in this work are gas liquid chromatography (GLC), mass spectrometry (MS), I H and 13C nuclear magnetic resonance (NMR).…”

Entwicklungstendenzen und neuere Ergebnisse der organischen Schwefelchemie

“…B. H 2S, S28. S02 [8], S03 [9]) und davon abgeleiteten Schwefel-Halogen-Verbindungen (z. B. SCl 2 [10], SOCI 2 [11]).…”

“…,10 Aber auch hier sind die Grenzen der Reaktion derzeit unklar, wie iiberhaupt S03 als Agens in der organischen Chemie nur sparlich untersucht wurde [9]. In diese Reihe gehoren auch die Trithiapentalene, die in den letzten J ahren sowohl von der theoretischen als aueh von der synthetisehen Seite her intensiver bearbeitet wurden [38].…”

Preparation, Use, and Safety of O-Mesitylenesulfonylhydroxylamine

“…However, MSH has been reported to be safely stored at 0 °C and is stable in dichloromethane solution . There are also reports of violent explosions when heated to 60 °C and that attempted vacuum drying of the pure crystalline compound at ambient temperature led to an instant decomposition…”