Neopentyl sulfide

Neopentyl sulfides have been prepared by alkylation of sodium sulfide with neopentyl tosylate in high-boiling polar solvents,4,5 or in low yields by reduction of alkyl 2,2-dimethylpropanethioate with the combination of lithium aluminum hydride and a large excess of boron trifluoride-etherate. ... 

Dineopentyl sulfide Neopentyl sulfide (8) Propane, l,l -thiobis-[2,2-dimethyl- (9) (51616-83-2)... 

Neopentyl sulfides, 58, 146 Neopentyl tosylate, 58, 147 Nickle cathode, 57, 92 Nickle(U) chloride hexahydrate, 58, 128 Nickel, dichlorobis(triphenylphosphine), 58, 133... 

Details for the preparation of phenyl neopentyl sulfide are available (equation... 

Phenyl neopentyl sulfide, 272 Phenyl oxime-O-sulfonates, 456 2-Phenyloxirane, 219 Phenylpropargyl aldehydes, 6 Phenylselenenyl bromide, 459-460 Phenylselenenyl chloride, 459-460 Phenylselenenyi trifluoroacetate, 459 Phenylselenlnyl chloride, 459-460 ot-Phenylseleno ketones, 459 Phenylselenol, 235, 362 Phenylsulfinylcarbene, 457... 

SULFIDE SYNTHESIS IN PREPARATION OF DIALKYL AND ALKYL ARYL SULFIDES NEOPENTYL PHENYL SULFIDE... 

The catalyst could be recovered (80-90%) from the distillation residue, which also contained some neopentyl phenyl sulfide... 

Dineopentyl and neopentyl phenyl sulfides are obtained from 1-bromo-2,2-dimethylpropane. Some other examples are given m Table I. 

Sulfide, neopentyl phenyl (8) Benzene, [(2,2-dimethylpropyl)thio]-(9) (7210-80-2)... 

Naphthoquinone, 2-methyl- 56,70 Neber reaction, 57, 87 Neopentylbromide, 58, 145 NEOPENTYL PHENYL SULFIDE, 58,... 

HEXAHYDRO - 4a,5 - DIMETHYL - 2(3H) - NAPHTHALE-NONE and 2-TRIMETHYLSILYLOXY-1,3-BUTADIENE AS A REACTIVE DIENE DIETHYL trans -4-TRIMETHYL-SILYLOXY-4-CYCLOHEXENE-1,2-DICARBOXYLATE. Sulfur substitution also continues to be of high interest, and three preparations on sulfide synthesis are included BENZYL SULFIDE DIALKYL AND ALKYL ARYL SULFIDES NEOPENTYL PHENYL SULFIDE and UNSYMMETRICAL DIALKYL DISULFIDES sec-BUTYL ISOPROPYL DISULFIDE. 

Thioethers (sulfides) can be prepared by treatment of alkyl halides with salts of thiols (thiolate ions).7S2 R may be alkyl or aryl. As in 0-35, RX cannot be a tertiary halide, and sulfuric and sulfonic esters can be used instead of halides. As in the Williamson reaction (0-12), yields are improved by phase-transfer catalysis.753 Instead of RS ions, thiols themselves can be used, if the reaction is run in benzene in the presence of DBU (p. 1023).754 Neopentyl bromide was converted to Me3CCH2SPh in good yield by treatment with PhS in liquid NH3 at -33°C under the influence of light.755 This probably takes place by an SrnI mechanism (see p. 648). Vinylic sulfides can be prepared by treating vinylic bromides with PhS in the presence of a nickel complex,756 and with R3SnPh in the presence of Pd(PPh3)4.757 R can be tertiary if an alcohol is the substrate, e.g,758... 

Very good yields, mild conditions, regioselectivity, versatility in the choice of the two reacting species (easy access to thermodynamic versus kinetic silyl enol ethers as well as to the required a-chloroalkyl phenyl sulfides) give to these sequences a particularly wide scope. Neopentylation is one illustration of their utility [325]. 

The reaction has also been realized in the gas phase with sulfur being generated by mixing sulfur dioxide with hydrogen sulfide.27,28 This method seems to be very efficient for the preparation of aromatic and aliphatic compounds as well as the unsubstituted l,2-dithiole-3-thione. More complex l,2-dithiole-3-thiones such as 17 have also been prepared.28 4-Neopentyl-5-t-butyl-l,2-dithiole-3-thione has been prepared from triisobutylene and sulfur.29 1-Phenyl-1-propene does not give a simple thione in the reaction with sulfur, but thiol 18. The yield was raised by the presence of hydrogen sulfide and benzoyl peroxide.30... 

---