Oxathiolane-3.3-dioxides

C3OS 0 S — — — 3,3-Diphenyl-1,2-oxathiolane 2,2-dioxide 5H-l,2-benzoxathiole 2,2-dioxide... 

Water-soluble PPEs have been made by the suitable choice of ionic and highly hydrophilic side chains. These PPEs will play a role in bio-type sensing applications (vide infra). A clever example is Schanze s synthesis of a sulfonato-substituted PPE [40, 41]. The NaOH-promoted reaction of [1, 2]oxathiolane-2,2-dioxide with 2,5-diiodohydroquinone gives a bis-sulfonate that can be coupled (Pd-catalyzed) to 1,4-diethynylbenzene to form a water-soluble PPE (Scheme 4) Table 6, entry 1). In a similar approach, Schanze et al. [42] made a... 

Chem. Abstr. Serv. Reg. No.-. 1120-71-4 Chem. Abstr. Name-. 1,2-Oxathiolane, 2,2-dioxide... 

Oxathiolane 2,2-dioxide undergoes metallation with n-butyllithium as expected at the 3-position (81JOC101). The anion may be alkylated with alkyl halides or carbonyl compounds. The isomeric 1,3-oxathiolane 3,3-dioxides also undergo metallation ortho to the sulfone and, when the 4-position is blocked, metallation at the 2-position may be used as an efficient conversion of alkyl halides into aldehydes as shown in Scheme 22 (79TL3375). 

The reaction of alkenes with sulfur trioxide is an important synthesis of 1,2-oxathiolane 2,2-dioxides. The best conditions involve the use of a dioxane-sulfur trioxide complex at low temperature. The initial addition involves formation of the most stable cation followed by ring closure, as shown in Scheme 31 (74JOC2459). 

With one important exception, dioxoles and oxathioles do not appear to be a particularly toxic class of compounds. The exception is 1,2-oxathiolane 2,2-dioxide (propane sultone) which produces brain tumors, leukaemias and adenocarcinomas of the small intestine in rats treated with 28 mg kg-1 orally twice a week for 60 weeks. If the toxicity is associated with its ability to act as an alkylating agent, then higher homologs should have similar, but reduced, carcinogenic potential. 

Hydrogen atom abstraction from 1,2-oxathiolane 2,2-dioxide (14) using, for example, OH- has been examined and is found to give a 2 1 ratio of the 4- and 5-radicals, both of whose ESR spectra have been recorded <75JCS(P2)1245>. 

The cyclic sulfites (104) undergo ring contraction upon treatment with BF3 EtjO to give the 1,2-oxathiolane 2,2-dioxides (105) (Equation (19)) <93TL3667>. Access to the 2,l-benzoxathiol-3-one... 

Oxaspiro [4,5] decane-7,9-dione. See 3,3-Tetramethylene glutaric acid 1,2-Oxathiolane, 2,2-dioxide. See 1,3-Propane sultone... 

CAS 1120-71-4 EINECS/ELINCS 214-317-9 Synonyms 3-Hydroxy-1-propanesulfonic acid sultone 3-Hydroxy-1-propanesulfonic acid y-sultone 1,2-Oxathiolane, 2,2-dioxide 1-Propanesulfonic acid-3-hydroxy-y-sultone Propane sultone Empirical CsHeOsS... 

Cyclic Sulphonates, Cyclic Sulphinates, and Related Systems.—A valuable new method of synthesizing 1,2-oxathiolan 2,2-dioxides and 1,2-oxathian... 

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