Vol. 73
-IS8 i TABLEI Molr of ihiol
A1.KY.I. i I N 1 1 A R Y L WOCTAIJECYI, S U L F I D E S &role of Solvent for I'icld, b MclLiv,: es1cr rccrpstallization" r; point, -C.
0 057
1 1 U50
101
,100
. 101
. 100
I'ctroleum ctlicr ( b . p 35-60') Acetone
Sulfur aiialyscs, < ' ( Calcd. I'outid
SO
5 5 . 5 - 3 ; .5
X.S4
8 i6
rj1
28-3!,l
x.51
8.58
x 21 x 19 Petroleum ether hj 3 2 .X i 3 (b p. 35-60") . IOU . IOU Acetonc. 71 29-:30 .103 ,100 Methyl ethyl ketone 70 44-45 ,104 ,100 hfcthyl ethyl ketone 7.3 50 5-31 .i Benzene lit' ti:j M X 3' ,105 100 (' 911 products werc rccrystallized once from ethanol or methanol and one or two times from the solvent listed i l l this coluinii. Thc ii1.p. of n-octadecyl sulfide has previously All yields are based on starting n-octadecyl p-toluenesulfonate. bc.cii reported as 62-0406 aiitl 98-09°.6 ziiibed aboic The pioduct, foiined in 57% yield, melted 61-62'. A n d . Calcd. for C L ~ H ~ L OS, Z S8.1%. : Found: S, 7 93. Di-n-octadecyl Sulfone.-Di-n-octadecyl sulfide (5.0 g . or 0.0093 mole) was oxidized as described previously. The product, m.p. 103-104', was formed in 43% yield. .lnal. Calcd. for C36H7402S: S, 5.61. Found: S, 5.46. The melting point of octadecyl sulfone has been reported previously as 98-99" and 105.5-106.5°.5 p-Aminophenyl la-Octadecyl Sulfone.-Three grams (0.0068 mole) of p-nitrophenyl n-octadecyl sulfone was reduced with 7.0 g. (0.031 mole) of stannous chloride in acetic acid in accordance with the procedure outlined above for the reduction of p-nitrophenyl la-octadecyl sulfide. There w;s obtained 2.0 g. (72% yield) of amine melting a t 110-1 12 . .Inal. Cdlcd. for CUH~~NOZS: S, 7.83. Found: S, 7.70. 19,22-Dithiatetracontane.-An attempt to produce the dithio ether from 1,2--ethanedithiol and two equivalents of - ______ At
fi) V C Barry I, O'Rourke and D Twomeny Proc Ros l r t s k 61B,223 (1947) ( 5 ) R A Hunter I o w a S t u / e C O ~ ~ C J KSt$, C 16, 216 (1911) jL .I 36, 1474 (1042)l Icad,
/ C ( J N I R 1 1 3 t I I V X I RUM I l l E I
