N-, O-, and S-Trihalomethyl Compounds

Sulfur, an Important Element in my Life

“…Much of the attention it has received derives from the commercial success of the fungicide captan (3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione) [64] which was prepared from it [65]. On careful analysis of commercial 2 we discovered that it contains the previously unobserved contaminant dichloromethanedisulfenyl dichloride, CC12(SC1)2, lla, the product of the photochlorination of carbon disulfide [66].…”

Sulfur, An Important Element in my Life

“…Much of the attention it has received derives from the commercial success of the fungicide captan (3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione) [64] which was prepared from it [65]. On careful analysis of commercial 2 we discovered that it contains the previously unobserved contaminant dichloromethanedisulfenyl dichloride, CCl 2 (SCl) 2 , 11a, the product of the photochlorination of carbon disulfide [66].…”

“…on sulfur-related subjects such as N-, O-and S-trihalomethyl compounds [65], sulfurcontaining reagents in organic synthesis [233], reactions of thiocarbonyl compounds with chlorine and with SCl 2 [98], carbon monosulfide [34,35], the chemistry of divinyl disulfides [234], 3-cyanopyridin-2(1H)-ones, -thiones and -selones [235], the synthesis of naturally occurring sulfinic acids [236], chlorodithioformates [125], 1,2-dithietes [237], ,-unsaturated isothiocyanates [238], carbon chloride sulfides [102], geminal disulfenyl dichlorides [101], dithiiranes-thiosulfines [21,239], and on non-sulfur subjects such as piracetam and other structurally related nootropics [18], synthesis and reactions of piracetam-type pyrrolidines [20], 2(5H)-furanones [240,241], and a popular account of drug development [242]. A collection of informal, minor reviews deals with the subjects of thiosulfenyl chlorides [243], dithiiranes-thiosulfines [244,245], triphenylmethanethiol-triphenylmethanesulfenyl chloride [246], sulfenyl and selenenyl azides [247], -thioxo sulfones and S-derivatives [248], tetrathioorthocarbonic acid and its derivatives [249], N,N 0 -di-tert-butylsulfur diimide [250], 1,2,4-thiadiazetidines [251], thio-, seleno-and telluroketenes [141] and thiophosgene S-oxide [252].…”

Acidity and reactivity of trifluoromethanesulfonic acid in liquid and solid acid catalysts

“…Trifluoromethanesulfonic acid (TFMSA or triflic acid) is known to be a strong acid suitable to be used as catalyst for synthetic applications [1][2][3][4][5][6][7][8][9]. The design of acid-catalysed reactions over solids has caused a pronunced need for further researchs in this area and supported triflic acid [10][11][12][13][14] or materials with -CF 2 SO 3 H groups [9,[15][16][17][18] are becoming now available to replace homogeneous acid solutions.…”