Sulfenyl chloride, formation from chlorine

Sandmeyer reaction, synthesis, of bromo compound, 36, 39, 45, 48, 52, 75, 217 of chloro compound, 48, 110, 113 of cyano compound, 90, 91, 216 of iodo compound, 182, 183, 184, 185 use of mercuric nitrate in, 52 Saponification of an ester, 113, 152 Schiemann reaction, 165, 167 Schotten-Baumann reaction, 145 Skraup reaction, 28, 85, 193, 204, 235 Sommelet reaction, 281 Sulfenyl chloride, formation from chlorine and disulfide, 214... 

A three-step reaction sequence starting from 3,4-dichloro-l,2,5-thiadiazole (81) led to the formation of the stable sulfur-nitrogen radical [l,2,5]thiadiazolo[3,4-fl ][l,3,2]dithiazol-l-ium (14). Treatment of thiadiazole (81) with two equivalents of Na2S afforded the sodium salt (82), which reacted with chlorine gas to furnish the sulfenyl chloride (83). The reaction of this intermediate (83) with trimethylsilyl azide yielded the salt (84), reduction of which afforded the novel pentalene analogue (14) as black needle-like crystals (Scheme 18) <89AG(E)920>. 

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