Organic Lab Reactions 267 - 290 EXPERIMENTAL PROCEDURES 294 Ethanol Deaminations 294 Hypophosphorous Acid Deaminations 294 m-Nitrotoluene from

CHAPTER 7 REPLACEMENT OF THE AROMATIC PRIMARY AMINO GROUP BY HYDROGEN NATHAN KORNBLUM Oberlin College* and Harvard University * CONTENTS INTRODUCTION .- . . . 263 USE OF ALCOHOLS 264 Influence of Substituents 264 Acid Used for Diazotization 271 Nature of the Alcohol 273 Influence of Water, Catalysts, and Other Substances 274 Temperature - 277 REDTTCTION WITH HYPOPHOSPHOROUS ACID 277 REDUCTION WITH ALKALINE FORMALDEHYDE 282 USE OP STABILIZED DIAZONIUM SALTS *" . . . 285 TREATMENT WITH SODIUM STANNITE 286 CONVERSION TO THE HYDRAZINE FOLLOWED BY OXIDATION 287 MISCELLANEOUS REDUCING AGENTS 288 COMPARISON OF THE VARIOUS DEAMINATION PROCEDURES 289 APPLICATIONS OF THE DEAMINATION REACTION 290 EXPERIMENTAL

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Unformatted text preview: 290 EXPERIMENTAL PROCEDURES 294 Ethanol Deaminations 294 Hypophosphorous Acid Deaminations 294 m-Nitrotoluene from 3-Nitro-4-aminotoluene 294 Toluene from o-Toluidine 295 7-Chlorohydrindone-l from 4-Amino-7-chlorohydrindone-l 295 1,3,5-Trinitrobenzene from 2,4,6-Trinitroaniline . . . ./ . 296 Triptycene from 2,5-Diaminotriptycene 297 Alkaline Formaldehyde Deamination 297 4-Methyldiphenyl Ether from 4-Methyl-4'-aminodiphenyl Ether . . . . 297 Sodium Stannite Deamination 298 l,3-Dimethyl-5-bromobenzene from l,3-Dimethyl-4-amino-5-bromoben-zene • • • • 298 * National Research Fellow, 1942-1943. Present address, Purdue University. 262...
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