Thionyl bromide chloride fluoride

Halides and Oxyhalides op Sulphur —Fluorides, Chlorides, Sulphur Bromide, Sulphur and lodino, Oxyfluorides, Oxychlorides, Thionyl Bromide. 

Thiocyanogen solution, 1 84, 86 standardization of, 1 86 Thionyl bromide, 1 113 Thionyl fluoride, 6 162 Thiophosphoryl bromide, 2 153 Thiophosphoryl chloride, 4 71 Thiophosphoryl triamide, 6 111 Thiosemicarbazide, 4 39... 

SFe Sulfur(VI) fluoride, 1 121 SH2 Hydrc en sulfide, 1 111 SOBr2 Thionyl bromide, 1 113 SO2 Sulfur dioxide, 2 160 SO2CI2 S dfuryl chloride, 1 114 S02 N(CH3)3 Trimethylamine-sulfur dioxide, 2 159 SOs CsHsN Pyridine-sulfur trioxide, 2 173... 

Thallium (ITT) fluoride has been prepared by the action of fluorine or bromine trifluoride on thaUium(III) oxide at 300°C. It is stable to ca 500°C but is extremely sensitive to moisture. Thallium (ITT) chloride can be obtained readily as the tetrahydrate [13453-33-3] by passing chlorine through a boiling suspension of HCl in water. It can be dehydrated with thionyl chloride. Thallium (ITT) bromide tetrahydrate [13453-29-7] is prepared similarly, whereas the iodide prepared in this manner is thaUium(I) triiodide [13453-37-7] H" F2-... 

Thiocarbonyl tetrachloride, i6, 21 Thionyl chloride, 45, 16, 98 Thiophosgene, 45, 21 Thiophosphoryl chloride, reaction with methylmagnesium bromide to yield tetramethylbiphosphine disulfide, 45,102 Toluenesulfonybromide, 46, 88 Trichloroacetyl fluoride, 46, 6 1,1,3-Trichloiio- -nonane, 46,104 Tricyclo[2.2.1.0 ]heptan-3-ol, 45,... 

The known thionyl hahdes include SOX2 (X = F, Cl, and Br Table 13) as well as the mixed compound SOFCl. They are pyramidal in geometry, with the S=0 bond being shorter in the fluoride than the chloride or bromide. Thionyl chloride is prepared industrially by reacting sulfin dioxide or trioxide with sulfin dichloride or sulfin monochloride, or by the reaction of phosphorus trichloride with sulfinyl chloride (equations 54 57). 

The thionyl halides range from 1308 cm for thionyl fluoride, through 1233 for thionyl chloride [52] to 1121 cm for the bromide [85]. Nitrogen substitution also raises s=o as there is no resonance. Sulphinamides have been studied by Smith and Wu [86], by Keat et al. [87] and by Steudel [84]. With A -alkyl groups on both sides of the sulphur atom the frequency is close to 1120 cm", but lower values are found for structures such as R—NHSO—R (1060—1037 cm" ) [86]. In these the bands are usually doubled which may indicate dimerisation as in the amides. Two sulphur atoms attached to the S=0 group give frequencies close to 1105 cm-i. 

The N-SES group can be incorporated by treating an aldehyde with iV-sulfinyl-/3-trimethylsilylethanesulfonamide (SESNSO) (13), which can be made by treating the sulfonamide (12) with thionyl chloride and a catalytic amount of M,fV-dichloro-/7-toluenesulfonamide (eq 7) (see also fV-sulfinyl-/7-toluenesulfon-amide. The iV-sulfonyl imine can be used in situ in a number of reactions. For example, the fV-sulfonyl imine from aldehyde (14) reacts with 2,3-dimethylbutadiene (eq 8) to give the Diels-Alder adduct (15). Treatment of (15) with fluoride ion affords the bicycUc lactam (16). Also, the fV-sulfonyl imine derived from isobutyraldehyde and (13) reacts with vinylmagnesium bromide to provide the allylic SES-sutfonamide (17) in 65% yield (eq 9). ... 

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