Electro-Organic Chemical Preparations. II

A paper presented at the Seventy-seventh Gen- eral Meeting, held at Wernersville, Pa., April 27, 1940, H. J. Creighton presiding.

E L E C T R O - O R G A N I C C H E M I C A L P R E P A R A T I O N S . II. l

By SHERLOCK SWANN, JR. fl

ABSTRACT.

This review is an extension of an earlier list ~ of electro-organic syntheses which should be of value as methods of preparat ion to in- clude li terature published before January, 1940. For the sake of clarity the subjects in this paper have been numbered exactly as in the previous one. A letter has been appended to the numbers of tables in- troducing new subject mat ter except where it occurs at the end of the paper.

Most of the l i terature in this paper before 1936 consists of incidental electrochemical preparat ions found in the experimental sections of organic chemical papers. This literature was not available when the last survey was writ ten.

A list of er ra ta and explanatory notes referr ing to the 1936 survey will be found at the end of this paper.

The results of the latest search are classified in the following tables :

PART I.

COUPLING.

TABLE I.

No new data since last publication. ~

1 Published by permission of the Director of the Engineer ing Exper iment Station, Univers i ty of Illinois, Urbana , Illinois. Manuscr ip t received December 15, 1939.

Research Associate Professor of Chemical Engineer ing, Univers i ty of Illinois. 3 Trans . Electrochem. Soc., 69, 287 (1935).

459

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498 SIIERLOCK SWANN, JR.

ADDENDA AND CORRECTIoNs TO FIRST PAPER. s

The following preparation should be included in this paper.

Electrolytic Reduction of a-(Trichloromethyl)-2-pyridine~thanol to a-(Dichloro- methyl) -2-pyridine~thanol.

O H~SO, O H H

Brand and Reuter ~ have carried out this reduction in about 50 per cent yield,

The yields in Table I and our own preparation in Table II are based on free acid. The rest are on total acid.

On Page 387* the name of the last product should be elcosane. On Page 388 the date of reference number 11 should be 1925. On Page 391 the acid is dilute HC1. On Page 395 the H and O H attached to the a carbon atom in the formula for

glucose should be reversed. On Page 397 the date of reference number 36 should be 1929. o-Nitrophenol

was reduced in alkaline solution. The latter part of the formula in the column of products third from the bottom of the page should read - - N H O C C H s .

On Page 406 Azo Salicylic Acid should be Benzene Azo Salicylic Acid. The formula should be

C O O H

This reduction is carried out with TiCh which is regenerated electro|ytically in a separate cell.

On Page 407 the name of the starting material at the bottom of the page should read a- (3, 4-Dimethoxy-phenyl) -a-acetoxy-~-nitropropanol.

On Page 417 the electrolytic reduction of cinnamic acid is carried out in alkaline solution.

On Page 418 the yield of N-ethyl-o-toluldine should be 67.5 per cent. The product was weighed as nitrosamine.

On Page 419, p-toluamine should be p-tolubenzylamine. On Page 423, N-methyl dihydroisoindole should be N-methyl phthalimidine. On Page 425 the bond of the lower nitrogen atom to the carbon atom on its

r ight in the formula for desoxycaffeine should be doubIe. On Page 429 the reference 112 should refer to Speyer and Popp. On Page 435 the CH groups in the upper right part of the product should be

part of the rings.

s.~ Ber., 72, 1668 (19.39). The page numbers refer to the preprint of this paper (Preprint 69-36). The corresponding

page numbers of Volume 69 are as follows: Preprint Volume Preprint Volume Preprint Volume

Page 387 289 Page 406 308 Page 419 321 Page 388 290 Page 407 309 Page 423 325 Page 391 293 Page 417 319 Page 425 327 Page 395 297 Page 418 320 Page 429 331 Page 397 299 Page 435 337



ELECTRO-ORGANIC CHEMICAL PREPARATIONS. II. 4 9 9

Resumen del artlculo: "Preparaciones Electro-org~nicas. II."

Esta lista de reacciones electro-org~nicas sint6ticas completa a una anterior, s Los grupos principales de reacciones son: Parte la, acopla- miento; 2a, oxidaci6n; 3a, reacciones con los hal6genos (incluyendo la oxidaci6n de azflcar, catalizada pot los hal6genos) ; y 4a, reducci6n.



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Electro-Organic Chemical Preparations. II