Synthesis of Macrocyclic Amides and Their Intermediate 2 : 1 and 3 : 2 Reaction Compounds from Diethyl Oxalate and Ethereal Oxygen-Containing Diamines

Naoaki Fukada; Tadashi Ohtsu; Masamichi Miwa; Masayuki Mashino; Yasuyuki Takeda

doi:10.1246/bcsj.69.1397

Synthesis of Macrocyclic Amides and Their Intermediate 2 : 1 and 3 : 2 Reaction Compounds from Diethyl Oxalate and Ethereal Oxygen-Containing Diamines

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.69.1397 ◽

1996 ◽

Vol 69 (5) ◽

pp. 1397-1401 ◽

Cited By ~ 15

Author(s):

Naoaki Fukada ◽

Tadashi Ohtsu ◽

Masamichi Miwa ◽

Masayuki Mashino ◽

Yasuyuki Takeda

Keyword(s):

Diethyl Oxalate ◽

Ethereal Oxygen

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ChemInform Abstract: Synthesis of Macrocyclic Amides and Their Intermediate 2:1 and 3:2 Reaction Compounds from Diethyl Oxalate and Ethereal Oxygen-Containing Diamines.

ChemInform ◽

10.1002/chin.199635169 ◽

2010 ◽

Vol 27 (35) ◽

pp. no-no

Author(s):

N. FUKADA ◽

T. OHTSU ◽

M. MIWA ◽

M. MASHINO ◽

Y. TAKEDA

Keyword(s):

Diethyl Oxalate ◽

Ethereal Oxygen

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Isobaric Vapor–Liquid Equilibrium Measurements of Binary Systems of Dimethyl Carbonate with Dimethyl Sulfoxide, Anisole, and Diethyl Oxalate at 101.3 kPa

Journal of Chemical & Engineering Data ◽

10.1021/acs.jced.0c00998 ◽

2021 ◽

Vol 66 (3) ◽

pp. 1367-1375

Author(s):

Yongzheng Song ◽

Yan Wang ◽

Xubin Zhang ◽

Wangfeng Cai

Keyword(s):

Dimethyl Sulfoxide ◽

Binary Systems ◽

Dimethyl Carbonate ◽

Diethyl Oxalate ◽

Liquid Equilibrium ◽

Vapor Liquid Equilibrium ◽

Vapor Liquid

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Studies on the formation of complex oxidation and condensation products of phenols. Part III. -Rearrangements of oxidation-reduction type in the diquinone group

Proceedings of the Royal Society of London. Series A, Containing Papers of a Mathematical and Physical Character ◽

10.1098/rspa.1933.0214 ◽

1933 ◽

Vol 143 (848) ◽

pp. 223-228 ◽

Cited By ~ 8

Keyword(s):

Hydroxyl Group ◽

Hydrogen Atoms ◽

Blue Colour ◽

Highly Active ◽

Oxidation Reduction ◽

Intramolecular Reactions ◽

Trimethyl Ether ◽

Free Hydroxyl ◽

Ethereal Oxygen ◽

Complex Oxidation

The diquinones have been but little investigated, and as they contain two condensed highly active quinonid systems it is to be anticipated that they should be capable of interesting intramolecular reactions. When heated to 210-215º, 4 : 4'-dimethoxydiquinone is rapidly converted into a red crystalline isomeride (yield, 90%), soluble in alkali with an intense blue colour, and yielding a mono-acetate indicating the occurrence of a free hydroxyl group. Two hydrogen atoms are taken up on reduction, and the phenolic product yields a triacetate and a trimethyl ether. It follows that of the four carbonyl oxygens of 4 : 4'-dimethoxydiquinone, one has been converted into a hydroxyl group, and another which does not exhibit any functional activity, is probably present as ethereal oxygen. These results led to formula (III) as representing the product of rearrangement.

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