The mass spectrum of 5-phenyl-1,3,4-oxathiazol-2-one

Electron ionization mass spectra of 3,4‐disubstituted‐1,2,4‐oxa(thia)diazole‐5(4H)‐thione(ones). Substituent effects on the mass spectrometric rearrangement of 3‐aryl‐4‐(p‐tolyl)‐1,2,4‐oxadiazole‐5(4H)‐thiones to the corresponding oxo compounds

“…The spectra of metastable ions decomposing in the first field-free region (B/E and B 2 /E linked scans) were also recorded using the VG ZabSpec mass spectrometer. (6), 165 (11), 159 (8), 149(25), 137 (15), 133 (7), 132(14), 131 (6), 118 (5), 117 (7), 116(13), 110 (7), 105 (11), 104 (15), 92 (5), 91(62), 90 (11), 89 (11), 79 (5), 78(14), 77 (15), 65(26), 64 (5), 63 (10), 52 (8), 51(13), 50(5.5), 41 (5), 39 (19), 27(6) 2 282 (M C ž , 100), 222(88), 221 (18), 208(4), 165(21), 159 (16), 149 (19), 137 (15), 133 (7), 132 (17), 131(5), 118 (5), 117 (11), 116 (10), 111 (5), 110 (8), 105(12), 104 (15), 91(59), 90 (9), 89 (10), 79 (5), 78(14), 77(14), 65(28), 63(8), 52 (7), 51 (10) (7), 179 (10), 171 (7), 169 (17), 165(26), 149 (7), 139 (10), 138 (6), 137(48), 136 …”

“…304 (M C ž , 38), 302 (M C ž , 100), 244(25), 242(76), 241(24), 228 (7), 181 (6), 179 (19), 171(5), 169(13), 166 (6), 165(54), 139 (11), 138 (9), 137(67), 136 (8), 133 (16), 132(42), 131 (11), 123(9), 122 (5), 121 (7), 113 (5), 111 (15), 110 (18), 105(24), 104(31), 103 (7), 102 (18), 92 (8), 91(97), 90(13), 89 (10), 79 (11), 78(31), 77(30. two fragments through a retro-1,3-dipolar cycloaddition. 9 -11 In general, EI fragmentation of aromatic 1,2,4-oxadiazole derivatives occurs in this way and gives a nitrile (RCN) and a nitrile oxide R 1 CNO .…”

“…C ž , 100), 253(25), 239(11), 207(23), 206(5), 193(7), 192(10), 190(16), 180(11), 166(6), 165(55), 164(5), 149(10), 148(7), 138(5), 137(42), 136(6), 132(40), 122(5), 117(5), 116(12), 110(17), 105(18), 104(27), 103(7), 102(19), 92(6), 91(56), 90(46), 89(12), 88(5), 79(9), 78(26), 77(29), 76(22), 75(17), 66(5), 65(37), 64(11), 63(25), 62(5), 60(5), 53(6), 52(17), 51(28), 50(21), 45(5), 43(6), 41(8), 39(31), 38(5), 30(13), 27(11) ), 165(33), 148(4), 137(10), 134(22), 133(93), 132(20), 117(5), 116(7), 107(6), 105(15), 104(16), 103(7), 102(10), 92(8), 91(88), 90(45), 89(15), 79(7), 78(16), 77(19), 76(18), 75(11), 65(60), 64…”

Sulfur, An Important Element in my Life

“…With benzamide 91a no reaction was observed unless the reaction mixture was heated and then 5-phenyl-1,3,4-oxathiazol-2-one 92a was formed, probably by hydrolysis of the intermediate N-[(trichloromethyl)thio]benzamide 93 to N-[(chlorocarbonyl)thio]benzamide 94 (with concomitant dehydration of an equivalent amount of amide to nitrile) which then cyclizes with elimination of HCl; cf. equation (34) [78,79]. SCHEME 9 A large number of 5-aryl-1,3,4-oxathiazol-2-ones 92 were obtained in this way while the analogous preparation of 5-alkyl-1,3,4-oxathiazol-2-ones required the addition of an equivalent amount of benzamide because the starting alkanamides apparently were unsuitable as the source of water for the required hydrolysis [79].…”