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Hass–Bender oxidation

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Montavon, M.; Lindlar, H.; Marbet, R.; Rüegg, R.; Ryser, G.; Saucy, G.; Zeller, P.; Isler, O. (1957). "Synthesen in der Carotinoid-Reihe. 11. Mitteilung. α,β-Ungesättigte Carbonylverbindungen aus Allylhalogeniden mittels Nitroparaffinen".
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Hass, Henry B.; Bender, Myron L. (1949). "The Reaction of Benzyl Halides with the Sodium Salt of 2-Nitropropane. A General Synthesis of Substituted Benzaldehydes".
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atom, it is instead an oxygen of the nitro itself that attacks the benzylic carbon. The
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Organic Syntheses Based on Name Reactions: A Practical Guide to 750 Transformations
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Bersohn, Malcolm (1961). "C versus O Alkylation in the Case of a Stable Cation".
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Although originally developed for benzyl compounds, the reaction also works for
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Hassner, Alfred; Namboothiri, Irishi (2012). "Hass–Bender carbonyl synthesis".
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The reaction process begins with the deprotonation of 2-nitropropane at the
76: 68: 88: 238: 211: 72: 285: 87:, where the deprotonated carbon of the nitroalkyl group is the 36: 120: 116: 100: 251: 139: 167:Comprehensive Organic Name Reactions and Reagents 341: 165:Wang, Zerong (2009). "Hass–Bender oxidation". 321: 83:to displace the benzyl halide. Unlike in the 328: 314: 197: 99:to produce a benzaldehyde, with dimethyl 224: 342: 280: 164: 119:halides, giving the respective α,β- 95:-benzyl structure then undergoes a 13: 75:. This compound then initiates an 14: 371: 55:, who first reported it in 1949. 284: 107: 59: 51:is named for Henry B. Hass and 245: 218: 191: 175:10.1002/9780470638859.conrr297 158: 144:. Elsevier. pp. 203–204. 133: 29:Hass–Bender carbonyl synthesis 1: 169:. Wiley. pp. 1335–1337. 126: 300:. You can help Knowledge by 7: 355:Organic oxidation reactions 10: 376: 279: 33:organic oxidation reaction 43:using the sodium salt of 267:10.1002/hlca.19570400516 360:Organic chemistry stubs 47:as the oxidant. This 25:Hass–Bender oxidation 239:10.1021/ja01470a022 212:10.1021/ja01173a066 97:pericyclic reaction 85:nitroaldol reaction 309: 308: 294:organic chemistry 184:978-0-471-70450-8 151:978-0-08-096630-4 27:(also called the 21:organic chemistry 16:Chemical reaction 367: 330: 323: 316: 288: 281: 271: 270: 261:(5): 1250–1256. 255:Helv. Chim. Acta 249: 243: 242: 233:(9): 2136–2138. 227:J. Am. Chem. Soc 222: 216: 215: 206:(5): 1767–1769. 200:J. Am. Chem. Soc 195: 189: 188: 162: 156: 155: 137: 121:enones and enals 111: 103:as a byproduct. 63: 375: 374: 370: 369: 368: 366: 365: 364: 340: 339: 337: 335: 334: 277: 275: 274: 250: 246: 223: 219: 196: 192: 185: 163: 159: 152: 138: 134: 129: 80: 53:Myron L. Bender 17: 12: 11: 5: 373: 363: 362: 357: 352: 350:Name reactions 333: 332: 325: 318: 310: 307: 306: 289: 273: 272: 244: 217: 190: 183: 157: 150: 131: 130: 128: 125: 113: 112: 78: 65: 64: 45:2-nitropropane 35:that converts 15: 9: 6: 4: 3: 2: 372: 361: 358: 356: 353: 351: 348: 347: 345: 338: 331: 326: 324: 319: 317: 312: 311: 305: 303: 299: 296:article is a 295: 290: 287: 283: 282: 278: 268: 264: 260: 256: 248: 240: 236: 232: 228: 221: 213: 209: 205: 201: 194: 186: 180: 176: 172: 168: 161: 153: 147: 143: 136: 132: 124: 122: 118: 110: 106: 105: 104: 102: 98: 94: 90: 86: 82: 74: 70: 62: 58: 57: 56: 54: 50: 49:name reaction 46: 42: 41:benzaldehydes 39:halides into 38: 34: 30: 26: 22: 336: 302:expanding it 291: 276: 258: 254: 247: 230: 226: 220: 203: 199: 193: 166: 160: 141: 135: 114: 92: 89:nucleophilic 66: 28: 24: 18: 344:Categories 127:References 81:2 reaction 71:to form a 73:nitronate 69:α carbon 31:) is an 181:  148:  37:benzyl 23:, the 292:This 117:allyl 101:oxime 298:stub 179:ISBN 146:ISBN 263:doi 235:doi 208:doi 171:doi 19:In 346:: 259:40 257:. 231:83 229:. 204:71 202:. 177:. 123:. 329:e 322:t 315:v 304:. 269:. 265:: 241:. 237:: 214:. 210:: 187:. 173:: 154:. 93:O 79:N 77:S

Index

organic chemistry
organic oxidation reaction
benzyl
benzaldehydes
2-nitropropane
name reaction
Myron L. Bender

α carbon
nitronate
SN2 reaction
nitroaldol reaction
nucleophilic
pericyclic reaction
oxime

allyl
enones and enals
ISBN
978-0-08-096630-4
doi
10.1002/9780470638859.conrr297
ISBN
978-0-471-70450-8
doi
10.1021/ja01173a066
doi
10.1021/ja01470a022
doi
10.1002/hlca.19570400516

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