ti07
ANTIGONADOTHOPINS. I
Septeniber, 1961
TABLE 1 TRIARY LETHAN OLS
OH
R3 l\l.p.,
Compd.
Calcd., H
7'----
7
7 -
Found,* H
Yo--
N i4.4 5.0 4.3 74.2 4.6 4.6 H 229-230 71.1 6.9 6.6 70.7 6.9 6.6 138-138.5 H (Et)2XC2H,O I1 74.9 5.,5 3.6 (0.2 5.3 3.4 H 2 13-2 14 p-c1 CsHsCHiO 111 i3,.5 5.2 ... 73.6 5.2 ... 180-18 1 H p-c1 H It85.6 5.0 ... 85.4 6.0 ... 203-204 €1 I€ tr CoHj H 132 3-133.5 H VI' CoHb i8.3 6.0 ... 78.1 t5.0 .,. H 122-123 0-F CcHi CH,O VI1 78.3 6.0 .,. i8.1 j.9 . .. 124-125 H CH,O CoH, ITI1I P-F i3.1 7.0 ... 73.4 7.1 ... 142-143 H 4-Py (Et)2XCIH,O IX P-F 73.6 7.0 6.7 73.4 7.1 6.9 134-135 H 4-Py 0-F (Etj,?rTC*H,O S 82.8 i.l . .. 107 5-108 5 6.9 , . . 83.0 €I CHI C6H6 CHsO XI 87.1 6.7 ... 8i.4 i.4 . .. 87-88 CH? H H XII" CsH6 82.2 6.0 . .. 82.2 5.8 ... H 88-89 H CsHj SI11 p-F 82.5 6.1 , . . 82.2 5.8 ... H 89 5-90 5 0-F H CsHj SIV H 87-88 H C,Hj H XVd 6.8 6.9 iO.i 6.6 6.8 123-126 70.4 H 4-Py p-c1 SVI (Et j2SCyHIO 5.2 4.4 i3.6 5.2 4.5 i3.6 148-148.5 H p-c1 2-Py H SVII 111-112 H H Cs& XVIII' CHaO 74.5 6.0 H 117-1 18 i4.6 5.6 p-e1 CsH5 XIX CHI0 * W. Schlenk and E. Bergmann, .inn., 464, a Microanalysis were performed by Dr. A. Steyermark and staff of these laboratories. C. Hell and F. Wiegandt, Ber., 37, 1431 (1904). 29 (1928). c A. W. Fort and J. L). Roberts, J . Ani. Chem. Soc., 78, 584 (1956). C. F. Koelsch, J . Am. Chenz. Soc., 54, 2490 (1932). no.
I
R,
CHIO
R3 4-Py 4-Py 4-Py 4-Py 4-Py CsHj
R2
p-e1 p-e1
Y
OC.
C
C
S
-_
TABLE I1 TRIARYLETHYLEKES
-J@=CY4pJR2
R, Co11rpd. no.
Y
12i
ss
p-C1
SXI SXII XXIII XSIVB XXV XSW XST'II XSVIII SXIXS
p-e1 p-c1 p-C1 p-C1 p-C1
H H 0-F
XXS
H 0-F
SSSI XXXII
p-F P-F
H H H H
H H H H
H H H H H CH,
13.p. (mln.) or imp., O C .
229-230 180-1 8 1 161-163 ea. 100 60-61 96-97 132.5-133.5 140-141 210-215 ( 0 . 2 ) 69-70 lY0-195(0.4j 182-185(0.25) ... 70-7 1 58-59 62-63 15~5-160(0.2j 192-195 (0.45) 200-205(0.25) 207-209 2t54-256
Calcd., %---
7 -
C
H
N
,---l,'ound, C
yc H
N
74.2 62.8 64.0 58.1 82.6 78.2
4.6 4.6 4.5 3.3 4.4 8.6 5.9 4.8 5 . 2 c1,12.2 4.8 4.8
i4.4 62.8 63.9 57.6 82.7 78.4
5.0 4.3 4.6 3.7 4.8 i.!) 6.1 4.7 5 . 4 C1, 12.4 5.0 4.8
90.0 77.0
5.i 6.9
90.3 ii.4
5.6 7.1
...
6.0
82.8 5,6 ... 83.0 5.9 ... 82.8 5.6 .., 82.8 5.6 ... 77.0 6.9 7.2 76.2 6.9 7.2 H XXXIII 88.0 6.7 ... 87.9 6.9 ... XXXIV H 87.6 5.5 ,_. 87.8 5.5 ... P-F 0-F 87.9 5.5 ... XXXV H 87.6 5.5 , , . H XSXVI CHI 93.3 6.T .,. 92.7 7.0 ... H XSXT'IIJ H 88.2 6.3 .,, 88.2 6.8 ... p-c1 SXXVIII H i8.8 5.3 .. , i8.,5 5.7 ... SSSIS p-e1 H 61.2 4.0 3.8 61.1 4.1 3.9 p-c1 61.2 4.0 3.8 SL H 61.8 4.1 4.2 Isomeric with S S I I , nieltirig Ixiiiit and aiialysis of C?"111tiC1?;0.H,C,0,~0.:jH90: C1, 8.4. Found: C1, 8.6. Istinieric*with S S I , iiielt,ing point and analysis of C,,H1,CISO.HyC,Oa. c 12Zelting point and analysis of C?aH?iCISaO~l .5HaCrOr.2H?0. W. T. Tadros, K. Farahat, anti J. XI. Itolmm [ J . C'hevi. Soc., 439 (1040)] reported n1.p. 76-77'. Isonieric. with XI,, rneltirig pciiiit and analysis of C18H14ClN.HBr,1 Isomeric with X X X I S ) melting point and analysis of ClsH1,CIS.HBr. Y See fuotriote d, Table 11. See footnote b Table 1. i See footnote d Table 1. j See footnote e Table I. (1
ina. The most active of these are listed in Table 111.
ExDerimental
