Journal of Synthetic Organic Chemistry, Japan

Stereoselective Reactions of 1, 3, 5-Trithiananion

Michio FUKUNAGA

1974Volume 32Issue 3 Pages 153-160
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.153

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Possibilities in Electroorganic Syntheses

Sigeru TORII

1974Volume 32Issue 3 Pages 161-183
Published: March 01, 1974
Released on J-STAGE: April 23, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.161

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Telomerization of Isobutylene with Carbon Tetrachloride and Synthesis of β β-Dimethylacrylic Acid from Its 1 : 1 Adduct (1, 1, 1, 3-Tetrachloro-3-methylbutane)

Toru SATO, Manabu SENO, Teruzo ASAHARA

1974Volume 32Issue 3 Pages 184-187
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.184

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Telomerization of isobutylene with carbon tetrachloride in the presence of copper salts- aliphatic amines as the initiator system was investigated, and the 1 : 1 adduct (1, 1, 1, 3-tetrachloro-3-methylbutane) was obtained in yields over 90 mol %, based on the isobutylene. Then the hydrolyses of 1 : 1 adduct with sulfuric acid were carried out under various reaction conditions.
From the results of these investigations, it was confirmed that β β-dimethylacrylic acid is prepared in a two-stage process from isobutylene in overall yield of 7080 mol %, based on isobutylene.

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The Heat-condensation Reaction of Thiophthalide and the Related Compounds

Satoru YADA, Kunio ITABASHI

1974Volume 32Issue 3 Pages 188-191
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.188

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Heat-condensation reaction of Phthalic Anhydride (1a) with Phthalide (2a) or the corresponding sulfur compounds (1b), (2b) were investigated.
The products were not only Biphthalide type compounds (3), but also much a condensed cyclic type isomer (4).
The yield and ratio of products were remarkably changed by the combination of sample and reacted condition.

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Synthesis and Reduction of 1, 1-Pentamethylene-3-nitroguanidine

Synthesis of 1, 1-Disubstituted-3-aminoguanidines (Part 3)

Hiroshige TOKU, Takako YAMASHITA, Setsuko NAKADA, Tamio NISHIMURA

1974Volume 32Issue 3 Pages 192-196
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.192

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1, 1-Pentamethylene-3-nitroguanidine (2) was synthesized by nitration of 1, 1-pentamethyleneguanidine (1) with nitric acid or potassium nitrate in conc. sulfuric acid.
On reduction of (2) with Zn-AcOH, (1), 1, 1-pentamethylene-3-nitroso-guanidine (3), unkown oil (4), ammonia and 1, 1-pentamethylene-3-aminoguanidine (5) were obtained. These results can be explained by the following two competitive reactions ; 1) Direct formation of (5) from (2), (2) Consecutive degradation reactions : (2)→ (3) → (4) → (1) +NH₂OH→NH₃.
Hydrogenation of (2) in the presence of Pd/C in hydrochloric acid and ethanol gave (1) in yields of 8186%. On hydrogenation of (2) in acetic acid, neutral and alkali solution, the degradation also occurred without forming (5) by the mechanism similar to the Zn-AcOH reduction.

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Hydroquinone Formation from the Cleavage of p-Diisopropylbenzene Dihydroperoxide by Gaseous Acids

Synthesis of Phenols from Propylene. IV

Takaari YUMOTO

1974Volume 32Issue 3 Pages 197-199
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.197

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Decomposition of p-diisopropylbenzene dihydroperoxide in a benzene solution by hydrogen chloride could be carried out quantitatively in a saturated benzene solution at the temperature range of 2040°C, and its yield was 9293%, while that of acetone was found in 7377%.
The formed hydroquinone was highly pure (98%).
Similar decomposition also took place by using SO₂. However, the decomposition by hydrochloric acid gas gave a better result.

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Reaction of Benzyl Halides with 2-Phenyl-5-oxazolone

Studies on Syntheses and Reactions of α, α-Disubstituted Amino Acids (1)

Hiroyoshi AKASHI

1974Volume 32Issue 3 Pages 200-203
Published: March 01, 1974
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.32.200

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The reaction of benzyl halides with 2-phenyl-5-oxazolone obtained by the dehydration of hippuric acid was carried out in dimethylformamide by use of 50% aqueous solution of potassium hydroxide as a base.
After hydrolysis of the reaction mixture, N-benzoyl-α-benzylphenylalanine (1) and its benzyl ester (2) were obtained, respectively, in about 40% and 10% yields.
Even when equimolecular amounts of both reactants were used, di substituted derivative (1) was a main product, and monosubstituted derivative (N-benzoyl-dl-phenylalanine) was not obtained, but it was obtained as a by-product by use of quaternary ammonium hydroxide as a base. Disubstituted derivative was obtained in good yield (65% or 59%) by the reaction of benzyl halide derivative having electron-withdrawing group such as p-nitrobenzyl bromide or p-cyanobenzyl bromide.

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