Dipropyl sulfide

Nishimura and coworkers57-59 studied the y-radiolysis of aqueous solutions of sulfoxide amino acids. Sulfoxide amino acids are the precursors of the flavors of onions (S-propyl-L-cysteine sulfoxide, S-methyl-L-cysteine sulfoxide and S-(l-propenyl)-L-cysteine sulfoxide) and garlic (S-allyl-L-cysteine sulfoxide). In studies on sprout inhibition of onion by /-irradiation it was found that the characteristic flavor of onions became milder. In the y-radiolysis of an aqueous solution of S-propyl-L-cysteine sulfoxide (PCSO)57,58 they identified as the main products alanine, cysteic acid, dipropyl disulfide and dipropyl sulfide. In the radiolysis of S-allyl-L-cysteine sulfoxide (ACSO) they found that the main products are S-allyl-L-cysteine, cysteic acid, cystine, allyl alcohol, propyl allyl sulfide and diallyl sulfide. The mechanisms of formation of the products were partly elucidated by the study of the radiolysis in the presence of N20 and Br- as eaq - and OH radicals scavengers, respectively. 

In the case of PCSO the addition of N20 leads to increased formation of cysteic acid, alanine and dipropyl sulfide and to a decrease in the yield of dipropyl disulfide. The addition of KBr decreases the yield of all the four products. These findings indicate that cysteic acid and alanine are formed by the reaction of OH radicals in parallel reactions as given in Figure 7. 

Symmetrical sulfides can be made from the alkyl halide and Na2S as the product from the first step is the monoanion needed to make the second C-S bond. The synthesis7 is just to combine the alkyl bromide with Na2S in ethanol dipropyl sulfide (R = Et) is formed in 91% yield from the bromide while dibenzyl sulfide (R = Ph) is made in 83% yield from benzyl chloride 25. 

C6H10O4 adipic acid 124-04-9 1.150E-K10 80.400 9112 C6H14S dipropyl sulfide 111-47-7 1.092E+10 79.060... 

C6H14S dipropyl sulfide 111-47-7 in benzene 1.601 1 11493 C7H1202 vinyl pivalate 3377-92-2 gas 1.844 2... 

Propyl Sulfide. 1,1 -Thiobispropane dipropyl sulfide. C6H14S mo] wt 118.24. C 60.94%. H 1194%. S 27.12%. CjHtS( 3IIj. Prepd from propyl bromide and an alcoholic soln of Na2S. 

Unsymmetrical double bonds, as in N02, —N=C, >S=0, also —C=N, are hardly attacked at all, nor are bonds that are susceptible to other reducing agents. For instance, diallyl sulfide can be converted into dipropyl sulfide without fission of the S—S linkage.110 Carbonyl groups are, however, reducible (see page 62). 

Dimethyl and dipropyl sulfide are obtained similarly in 60% yield. 

---