2- -1,3,2-dioxathiolane

Dicyano-l,2,3-trithiole 2-oxide (143) has been prepared from the silver salt of 2,3-dimercaptomaleonitrile (142) and thionyl chloride (66HC(2l-i)67). Similarly, the reaction of ethylene glycol (144) with thionyl chloride gave 1,3,2-dioxathiolane 2-oxide (145), the parent compound of saturated five-membered cyclic sulfites (see Chapter 4.33). 

Dioxathiolane 2,2-dioxide, 4,4,5,5-tetramethyl-dipole moment, 6, 865 <77IZV98)... 

Dioxathiolane 2-oxide, 4,5-dimethyl-electron diffraction, 6, 857 <75BSB775)... 

Ethylene, /3-(dimethylamino)-nitro-in pyrrole synthesis, 4, 334 Ethylene, dithienyl-in photochromic processes, 1, 387 Ethylene, furyl-2-nitro-dipole moments, 4, 555 Ethylene, l-(3-indolyl)-2-(pyridyl)-photocyclization, 4, 285 Ethylene, l-(2-methyl-3-indolyl)-l,2-diphenyl-synthesis, 4, 232 Ethylene, (phenylthio)-photocyclization thiophenes from, 4, 880 Ethylene carbonate C NMR, 6, 754 microwave spectroscopy, 6, 751 photochemical chlorination, 6, 769 synthesis, 6, 780 Ethylene oxide as pharmaceutical, 1, 157 thiophene synthesis from, 4, 899 Ethylene sulfate — see 2,2-dioxide under 1,3,2-Dioxathiolane... 

Dioxathiolane oxides as epoxide equivalents and versatile synthons 98AHC(68)89. 

A review of cyclic sulfites and sulfates in organic synthesis includes many examples of 1,3,2-dioxathiolane 5-oxides and 5,5-dioxides <0OT7O51>. Reaction of cyclic sulfates such as... 

Significant advances in the chemistry of these ring systems over the past 10 years include the first unambiguous detection, and characterization by microwave spectroscopy as 1,2,3-trioxolane, of the primary ozonide from ethene and ozone (cf. Section 4.15.3.2), and the introduction of 1,3,2-dioxathiolane 2,2-dioxides as epoxide equivalents in organic synthesis (cf. Section 4.15.5.3). Advances have also been made in the synthesis and characterization of the chemistry of 1,2,3-trithiolanes and 1,2,3-trithioles. 

Table 1 Structural parameters of derivatives of 1,2,3-trithiolane, 1,3,2-dioxathiolane and 1,2,5-oxadithiolane and some unsaturated counterparts, obtained by x-ray or ... 

---