the action of nitrous acid on phenyl-α-(β-naphthol)-aminomethane. a correction

Dec., 1932 COMMUNICATIONS TO THE EDITOR 4753 tions of this reaction to all the non-polar inorganic halides and will be reported as rapidly as possible. MORLEY CHEMICAL LABORATORY WESTERN RESERVE UNIVERSITY CLEVELAND, OHIO HAROLD SIMMONS BOOTH CARL F. SWINEHART RECEIVED OCTOBER 22, 1932 PUBLISHED DECEMBER 13, 1932 THE ACTION OF NITROUS ACID ON PH.ENYGa-(P-NAPHTHOL)-AMINO- METHANE. A CORRECTION Sir : In a recent paper [Ray, THIS JOURNAL, 54,295 (1932) ] it was reported that phenyl-a-( p-naphthol)-aminomethane on treatment with nitrous acid gave an aliphatic diazo compound. Subsequent work, the details of which are soon to appear, has shown that the reaction is much more complex than was originally supposed. The compound in question is not an aliphatic diazo compound but an N-nitroso derivative of a hetero- cyclic compound. CHEMICaL LABORATORY UNIVERSITY OF CINCINNATI CIXCINNATI, OHIO RECEIVED OCTOBER 31, 1932 PUBLISHED DECEMBER 13. 1932 FRANCIS EARL RAY THE ACTION OF SODIUM IN LIQUID AMMONIA ON DERIVATIVES OF OPTICALLY ACTIVE TRIARYLMETHANES Sir: In view of a recent publication by Ashley and Shriner [THIS JOURNAL, 54, 4410 (1932)] on an attempt to prepare an optically active salt of the type [Rl:::Ra]-Na+ it seems advisable to place on record certain experiments which have been conducted in this Laboratory, and which were reported to the Society at its meeting in New Orleans, March 28- April 1, 1932. In recent publications from this Laboratory a method has been de- scribed for preparing certain derivatives of optically active triarylmethanes. Investigations of such optically active compounds led us to believe that a study of their behavior toward sodium in liquid ammonia should be of special interest. For this purpose 12-phenyl-l2-~-benzoxanthenethio- glycolic acid (I), m. p., 187-188', has been prepared. The pure levo modification of this compound (m. p. 184-185 ") prepared by repeated crystallization of its brucine salt gave [a12 in acetone -48.5'. This mate- \C/" rial in liquid ammonia was treated with metallic sodium CsH/\SCH&OOH sodium triarylmethyl so formed was allowed to react with a slight excess (yO'Q in the absence of oxygen. The deep orange-brown (1)

Upload: francis-earl

Post on 04-Feb-2017

212 views

Category:

Documents

0 download

Report

Download

Embed Size (px):

TRANSCRIPT

Page 1: THE ACTION OF NITROUS ACID ON PHENYL-α-(β-NAPHTHOL)-AMINOMETHANE. A CORRECTION

Dec., 1932 COMMUNICATIONS TO THE EDITOR 4753

tions of this reaction to all the non-polar inorganic halides and will be reported as rapidly as possible.

MORLEY CHEMICAL LABORATORY WESTERN RESERVE UNIVERSITY CLEVELAND, OHIO

HAROLD SIMMONS BOOTH CARL F. SWINEHART

RECEIVED OCTOBER 22, 1932 PUBLISHED DECEMBER 13, 1932

THE ACTION OF NITROUS ACID ON PH.ENYGa-( P-NAPHTHOL)-AMINO- METHANE. A CORRECTION

Sir : In a recent paper [Ray, THIS JOURNAL, 54,295 (1932) ] i t was reported

that phenyl-a-( p-naphthol)-aminomethane on treatment with nitrous acid gave an aliphatic diazo compound. Subsequent work, the details of which are soon to appear, has shown that the reaction is much more complex than was originally supposed. The compound in question is not an aliphatic diazo compound but an N-nitroso derivative of a hetero- cyclic compound.

CHEMICaL LABORATORY UNIVERSITY OF CINCINNATI CIXCINNATI, OHIO RECEIVED OCTOBER 31, 1932 PUBLISHED DECEMBER 13. 1932

FRANCIS EARL RAY

THE ACTION OF SODIUM IN LIQUID AMMONIA ON DERIVATIVES OF OPTICALLY ACTIVE TRIARYLMETHANES

Sir: In view of a recent publication by Ashley and Shriner [THIS JOURNAL,

54, 4410 (1932)] on an attempt to prepare an optically active salt of the

type [Rl:::Ra]-Na+ it seems advisable to place on record certain

experiments which have been conducted in this Laboratory, and which were reported to the Society at its meeting in New Orleans, March 28- April 1, 1932.

In recent publications from this Laboratory a method has been de- scribed for preparing certain derivatives of optically active triarylmethanes. Investigations of such optically active compounds led us to believe that a study of their behavior toward sodium in liquid ammonia should be of special interest. For this purpose 12-phenyl-l2-~-benzoxanthenethio- glycolic acid (I), m. p., 187-188', has been prepared. The pure levo modification of this compound (m. p. 184-185 ") prepared by repeated crystallization of its brucine salt gave [a12 in acetone -48.5'. This mate- \C/" rial in liquid ammonia was treated with metallic sodium CsH/\SCH&OOH

sodium triarylmethyl so formed was allowed to react with a slight excess

(yO'Q in the absence of oxygen. The deep orange-brown (1)

Separation of 1,1'-bi-2-naphthol enantiomers by continuous

Barritt Reagent A (for VP test)Barritt Reagent A (for VP test) R029 Ingredients a-Naphthol (1-Naphthol) 5.000 gm Absolute ethanol 100.000 ml **Formula adjusted, standardized to suit

ELECTROCHEMICAL DEGRADATION OF NAPHTHOL AS-BO … _Muji... · 2019-01-29 · Journal of Chemical Technology and Metallurgy, 52, 6, 2017 1116 ELECTROCHEMICAL DEGRADATION OF NAPHTHOL

IS NIR Spectra (2045 spectra) · 2-Naphthaldehyde 2-Naphthoic acid 2-Naphthol 2-Naphthol-6,8-disulfonic acid 2-Naphthylamine-3,6-disulfonic acid 2-Naphthylamine-4,8-disulfonic acid

Synthesis of Phenyl-2-Propanone (P2P)

Temperature-Dependent Kinetics of Phenyl Acetate … Hawkins, and Tester 4 Figure 3: Overall Reaction scheme for the base-catalyzed hydrolysis of phenyl acetate. Phenyl acetate undergoes

Kinetics and Mechanism of the Oxidation of Naphthol Green B by

Mechanistic Investigation of Oxidation of Phenyl

Opinion on phenyl methyl pyrazolone€¦ · 3-methyl-1-phenyl-2-pyrazoline-5-one 3-methyl-1-phenyl-5-pyrazolone 3.1.1.3. Trade names and abbreviations Phenyl methyl pyrazolone Norantipyrine

PHENYL ETHYL FORMATE (Code: PEF)