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Results and Discussion the 4-Bromophenacyl Esters 6 (Table VII)

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Results and Discussion the 4-Bromophenacyl Esters 6 (Table VII) A Convenient Preparation of Anhydrous Alkali Metal Thiocarboxylates Shinzi Kato*, Motohiro Oguri, and Masaru Ishida Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-11, Japan Z. Naturforsch. 38b, 1585-1590 (1983); received July 5, 1983 Lithium Thiocarboxylates, Sodium Thiocarboxylates, Potassium Thiocarboxylates, Rubidium Thiocarboxylates, Caesium Thiocarboxylates A series of alkali metal thiocarboxylates (1-5) were found to be readily obtained in high yields by the reaction of thiocar boxy lie acids with metal hydrides (LiH, NaH, KH), and rubidium or caesium acetates, respectively. Their physical properties were disclosed. Alkali metal salts of thiocarboxylic acid, espe- cially lithium thiocarboxylates (la-e), sodium 2- cially anhydrous salts, are of the most important methyl- (2c), 3-methyl- (2d), and 2-chlorothio- starting materials. However, only a limited amount benzoates (2f), and rubidium 2-methylthiobenzoate of information on their preparation and spectral (4 c) are too strong hygroscopic (deliquescent) to data has been available because of their strong carry out their microanalyses. The lithium salts (1) hygroscopicity [1]. Recently, the convenient prep- are soluble in ether, but less soluble in chloroform. aration methods of a series of anhydrous alkali Surprisingly, alkali metal thiocarboxylates except metal dithiocarboxylates were developed [2]. This the lithium salts (1), especially in an anhydrous result stimulated us to develop similar convenient solid state, show very strong static electrical prop- methods for the preparation of anhydrous alkali erties. This is in sharp contrast to alkali metal metal thiocarboxylates and to compare their phys- carboxylates, which do not show such a property. ical properties. The structures of 1, 2, 3, 4, and 5 obtained here were established by IR and UV spectral data, and elemental analysis (Table VI), or by conversion to Results and Discussion the 4-bromophenacyl esters 6 (Table VII). Preparation For the preparation of lithium (1), sodium (2), IR spectra and potassium thiocarboxylates (3), the reactions As shown in Tables I-V, the vasC=0 vibrations of of thio acids with lithium-, sodium-, and potassium most of the salts are observed in the region of hydrides were found to give high yields. In con- trast, the use of lithium, sodium, and potassium O metals is impractical, because of their low reactivity LiH II RCSLi (1) and of covering of these metals by the product [3]. 1 Rubidium- (4) and caesium thiocarboxylates (5) have been obtained, however, by using rubidium O NaH II and caesium acetates as the metal sources [4]. The RCSNa (2) reaction conditions, yields, and spectral data are 2 collected in Tables I-V. O O The alkali metal thiocarboxylates (1-5), except II KH II caesium thioacetate (5 a), are thermally stable in RCSH ->• RCSK (3) 3 the solid state and did not change within 6 months or more at room temperature. In general, the li- O thium (1) and sodium salts (2) are strong hygro- CH3C02Rb II >• RCSRb (4) scopic, as compared with the corresponding potas- 4 sium (3), rubidium (4) and caesium salts (5). Espe- O CH3C02Cs II • RCSCs (5) * Reprint requests to Dr. S. Kato. 5 0340-5087/83/1200-1585/$ 01.00/0 Scheme 1. Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. 1586 S. Kato et al. • A Convenient Preparation of Anhydrous Alkali Metal Thiocarboxylates 1450-1540 cm-1, as characteristic intense bands. Experimental Ring substitution by methyl, methoxy or nitro Melting points were determined using a Yanagi- group or chlorine atom in the ortho-, meta-, and moto micro melting point apparatus and are un- , , , f ,u corrected. The IR spectra were measured on a para-position does not cause large shifts of the JASC0 grating IR s£ectrophotometer IR.G. The carbonyl stretching vibration. UV and Visible spectra were obtained with a Table I. Physical properties of lithium thiocarboxylates (1). No. RC(0)SLi Time Solvent Method3, Yield13 M.p.c IR [cm-1]d UV [nm]e [%] R [h] n-C6Hi4/Et20 [°C] fasC = 0 Amax (log e) la CöHS 24 5:1 A 100 206 1509 282 (3.65) 286 sh (3.64) lb 4-CH3C6H4 42 5:1 B 49 157 1500 241 (3.93) 284 (3.74) 286 sh (3.73) lc 4-ClC6H4 18 5:1 B 67 191 1481 239 (3.81) 1496 290 sh (3.50) 299 (3.53) ld 4-CH3OC6H4 20 2:1 A 33 132 1502 256 (3.88) 293 (3.81) le 4-N02C6H4 20 1:1 A 80 93 1512 262 (3.92) 354 (3.50) a A = the use of excess thio acid, B = the use of excess of LiH; b isolated yield; c decomposition; d KBr; e EtOH. Table II. Physical properties of sodium thiocarboxylates (2). No. RC(0)SNa Time Solvent Yield3 M.p.b IR [cm-1]0 UV [nm]d [%] R [h] n-C6Hi4/Et20 [°C] VasC=0 A max (log e) 2a CH3 20 1:10 90 173 1517 249 (3.47) 1551 1562 2b CÖHÖ 18 10:1 66 217 1521 282 (3.65) 295 (3.63) 2c 2-CH3C6H4 20 2:1 92 64(?) 1524 258 (3.69) 2d 3-CH3CeH4 18 2:1 100 197 1505 284 (3.71) 294 sh (3.65) 2e 4-CH3C6H4 18 10:0 87 206 1502 285 (3.81) 299 (3.80) 2f 2-ClC6H4 20 2:1 84 67 ( ?) 1527 255 sh (3.72) 2g 3-CLCGH4 20 2:1 85 214 1502 288 (3.56) 295 sh (3.53) 2h 4-ClC6H4 20 1:1 86 259 1504 288 (3.72) 297 (3.76) 2i 4-CH3OC6H4 18 2:1 55 213-218 1506 258 (3.97) 1519 294 (3.90) 4-N02C6H4 18 1:1 98 222 1491 260 (4.04) 2j 1521 a The isolated yield; b decomposition; c Nujol; d EtOH. 1587 S. Kato et al. • A Convenient Preparation of Anhydrous Alkali Metal Thiocarboxylates Table III. Physical properties of potassium thiocarboxylates (8). No. RC(0)SK Time Solvent Yielda M.p.b IR [cm-1]0 UV [nm]d [%] R [h] n-C6Hi4/Et20 [°C] VasC = 0 Amax (log e) 3a CH3 76 0:10 79 131 1528 249 (3.90) 3b C6H5 20 4:1 81 202 1523 283 (3.75) 295 (3.74) 3c 2-CH3C6H4 44 1:1 84 40 1502 260 (3.66) 1532 3d 3-CH3C6H4 18 4:1 97 184 1532 291 (3.63) 296 sh (3.57) 3e 4.CH3C6H4 18 5:1 92 210 1516 283 (3.84) 293 (3.84) 3f 2-ClC6H4 68 1:2 85 148 1512 232 sh (4.02) 255 (3.92) 3g 3-CIC6H4 43 0:10 99 248 1526 288 (3.83) 299 sh (3.79) 3h 4C1C6H4 18 2:3 96 210 1523 290 sh (3.78) 298 (3.80) 3i 4-CH3OC6H4 68 1:3 74 176 1509 257 (4.09) 291 (4.02) 3j 4-N02C6H4 68 0:10 48 196 1520 259 (4.11) 340 (3.74) a The isolated yield; b decomposition; c Nujol; d EtOH. Table IV. Physical properties of rubidium thiocarboxylates (4). No. RC(0)SRb Time Solvent Yielda M.p.b IR [cm-1]0 UV [nm]«1 [%] R [h] n-C6Hi4/Et20 [°C] faSC = 0 Amax (log e) 4a CH3 50 0:10 94 206 1525 250 (3.69) 4b CßHÖ 17 2:1 99 143 1520 282 (3.63) 296 (3.62) 4c 2-CH3C6H4 44 1:4 79 94 1532 256 (3.81) 1543 4d 4-CH3C6H4 44 1:1 99 185 1527 286 (3.78) 294 sh (3.74) 4e 4-CH3C6H4 14 4:1 99 198 1524 283 (3.85) 294 (3.84) 4f 2-ClC6H4 44 1:4 81 127 1510 247 sh (4.17) 4g 3-CIC6H4 68 0:10 77 208 1529 288 (4.14) 297 sh (4.11) 4h 4-ClC6H4 44 1:2 98 232 1523 291 sh (3.73) 300 (3.76) 4-CH3OC6H4 60 1:2 94 118 1512 293 (3.92) 4i * 4j 4-N02C6H4 68 0:10 95 196 1520 259 (4.11) 340 (3.74) a The isolated yield; b decomposition; c Nujol; d EtOH. 1588 S. Kato et al. • A Convenient Preparation of Anhydrous Alkali Metal Thiocarboxylates Hitachi 124 spectrophotometer. Elemental analyses hydride (20 — 25% in oil) was purchased from Alfa were performed by the Elemental Analysis Center products. Rubidium and caesium acetates were of Osaka University, and Alfred Bernhardt Ana- commercial grade and dried under reduced pressure lytical Laboratory, Engelskirchen (Germany). at 140 ~ 150 °C. 4-Bromophenacyl bromide and thio- acetic acid are commercial grade and used without Materials further purification. Other thiocarboxylic acids were Lithium and sodium hydrides were reagent grade prepared by acidolysis of the corresponding piperi- and the former was triturated before use. Potassium dinium [5] or potassium thiocarboxylates [2 b] with Table V. Physical properties of caesium thiocarboxylates (5). No. RC(0)SCs Reaction Solvent Yielda M.p.b IR [cm-1]0 uv k [%] R Time [h] n-C6HI4/Et20 [°C] VasC = 0 A max (log e) 5a CH3 73 0:10 94 147 1520 249 (4.02) 5b C6H5 18 5:1 95 159 1526 282 (3.76) 293 (3.75) 5c 2-CH3C6H4 44 2:5 98 111 1492 259 (3.74) 5d 3-CH3C6H4 68 1:1 94 181 1528 285 (3.81) 294 sh (3.75) 5e 4-CH3C6H4 18 4:1 96 194 1523 242 (4.06) 283 (3.93) 291 sh (3.91) 5f 2-ClC6H4 66 1:3 97 134 1481 242 (3.73) 1502 252 sh (3.72) 5g 3-ClC6H4 44 0:10 88 173 1529 289 (3.95) 296 sh (3.93) 5h 4-ClC6H4 24 2:3 95 187 1520 241 (4.02) 289 sh (3.72) 299 (3.75) 5i 4-CH3OC6H4 68 1:2 91 168 1514 257 (4.07) 292 (3.99) 5j 4-N02C6H4 68 0:10 70 158 1513 259 (4.00) 1573 338 (3.65) a The isolated yield; b decomposition; c Nujol; d EtOH.
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