CiNii Articles - O-S rearrangement

1

Thio-Sugars.IV.Synthesis of Carbohydrate 1, 3-Glycol (Six-Membered) Thionocarbonates and Their Attempted O-S Rearrangement

TSUDA Yoshisuke , NOGUCHI Shinsuke , NIINO Hideki

… Four six-membered cyclic thionocarbonates (two sec-sec and two prim-sec) were prepared and their radical-promoted O-S rearrangement reaction was examined. … The results revealed that the reaction in six-membered rings is difficult compared with the simple rearrangement in five-membered rings. …

Chemical & pharmaceutical bulletin 49(9), 1210-1213, 2001-09-01

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2

Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring : Formation of cis-Arranged Cyclic Thiolcarbonates

TSUDA Yoshisuke , NOGUCHI Shinsuke , KANEMITSU Kimihiro , SATO Yoshiyuki , KAKIMOTO Kyoko , IWAKURA Yumiko , HOSOI Shinzo

… Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in accepTable yields.2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). …

Chemical & pharmaceutical bulletin 45(6), 971-980, 1997-06-15

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3

Phenol-Catalyzed Thione-Thiol Rearrangement of Xanthates and Modified Intermediate Neglect of Differential Overlap (MINDO/3) Analysis of the Reaction Mechanism

HARANO Kazunobu , KIYONAGA Hideo , HISANO Takuzo

… S-Alkyl dithiocarbonates (xanthates) of alkanols containing strained σ bonds underwent rearrangement to S, S-dialkyl dithiocarbonates, catalyzed by phenolic compounds. … The rate contants are proportional to the square of the concentration of phenol.The modified intermediate neglect of differential overlap (MINDO/3) geometry optimization indicates that S, S-dialkyl dithiocarbonate is ca. …

Chemical & pharmaceutical bulletin 40(10), 2654-2662, 1992-10-25

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4

Thermal Elimination of Carbonyl Sulfide from O-Aryl Thionocarbonates of Pyrrolidine-, Piperidine-, and Tetrahydrothiophene-2-ethanol

SAKANOUE Satomi , HARASAWA Shinya , YAMAZAKI Naoki , YONEDA Ryuji , KURIHARA Takushi

… Pyrolysis of O-2-(1-benzyl-2-pyrrolidinyl and 2-piperidyl)ethyl O-phenyl thionocarbonates (4 and 25) in acetonitrile gave 1-benzyl-4-phenoxyhexahydro-1H-azepine (7) and 1-benzyl-4-phenoxyoctahydroazocine (26) with liberation of COS in 55% and 32% yields, accompanied with 2-(2-phenoxyethyl)pyrrolidine and piperidine (8 and 27), via the azetidinum intermediate (6). …

Chemical & pharmaceutical bulletin 38(11), 2981-2985, 1990-11-25

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5

Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates by Pyridine N-Oxides.The Reaction Mechanism

HARANO Kazunobu , SHINOHARA Ikuo , SUGIMOTO Shin-ichiro , MATSUOKA Toshikazu , HISANO Takuzo

… The reaction of O-alkyl S-methyl dithiocarbonates (xanthates) (I) with pyridine N-oxides (II) gave the corresponding S-alkyl S-methyl dithiocarbonates (dithiolcarbonate) (III) together with the symmetric S, S-dialkyl and S, S-dimethyl dithiocarbonates in good yieds. …

Chemical & pharmaceutical bulletin 37(3), 576-581, 1989-03-25

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6

Reaction of Cyclic Thioxocarbonates with Tributyltin Hydride(Organic,Chemical)

KANEMITSU KIMIHIRO , TSUDA YOSHISUKE , HAQUE MOHAMMED EKRAMUL , TSUBONO KOJI , KIKUCHI TOHRU

… Treatment of methyl 2-О-acetyl-3,4-О-thiocarbonyl-β-L-arabinopyranoside with tributyltin hydride produced seven compounds, depending on the reaction conditions: the deoxy derivatives (2 and 3), the methylidene derivative (4), the carbonate (5), the О,S-rearrangement products (7 and 8), and the 4-deoxy acetyl migration product (9). …

Chemical & pharmaceutical bulletin 35(9), 3874-3879, 1987-09-25

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7

TRIALKYLTIN RADICAL USED TO CATALYZE THE O,S-REARRANGEMENT OF CYCLIC THIONOCARBONATES. A NEW ENTRY TO THIO-SUGARS(Communication to the Editor)

Tsuda Yoshisuke , Kanemitsu Kimihiro , Kakimoto Kyoko , Kikuchi Tohru

… The cyclic thionocarbonates give O,S-rearrangement products, the thiolcabonates, in appreciable yields, when treated with a catalytic amount of tributyltin hydride and α,α-azobisisobutyronitrile. …

Chemical & pharmaceutical bulletin 35(5), 2148-2150, 1987-05-25

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8

Heteroatom rearrangement. [in Japanese]

YOKOYAMA Masataka

… New heteroatom rearrangements are described : "S, N-, O, N-, and N, N-rearrangements" take place to afford the corresponding 1, 3-thiazines, 1, 3-oxazines, and pyrimidines when 3-alkyl-heteroatom group (MeS or MeSe) -3-heteroatom group (SH, OH, or NHPh) substituted acrylonitriles condense with carboxylic acids in the presence of dehydrating agents such as PPE, PPSE, phosphorus oxychloride, and 1-propanephosphonic acid cyclic anhydride. …

Journal of Synthetic Organic Chemistry, Japan 44(8), 767-781, 1986

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9

Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates. IV. Use of Boron Trifluoride Etherate as Catalyst

KOMAKI KEIJI , KAWATA TOSHINOBU , HARANO KAZUNOBU , TAGUCHI TANEZO

… Migration of alkyl group from O to S in the reaction of O, S-dialkyl dithiocarbonates with boron trifluoride etherate was studied to elucidate the reaction mechanism on the basis of results from kinetics, crossover reaction, and products formed. …

Chemical & pharmaceutical bulletin 26(12), 3807-3814, 1978-12-25

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10

Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates. III. The Reaction Mechanism [in Japanese]

KAWATA TOSHINOBU , HARANO KAZUNOBU , TAGUCHI TANEZO

… An experiment was carried out to confirm the reaction mechanism involving the formation of a carbonium ion which had been postulated previously for the catalytic rearrangement of O, S-dialkyl dithiocarbonates to S, S-dialkyl dithiocarbonates with Lewis acid. …

Journal of the Pharmaceutical Society of Japan 98(5), 600-604, 1978-05-25

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11

Reactions of alkyl diphenylphosphinates and related thio esters with some nucleophiles. SN2 (S) reaction and Wittig type rearrangement.

Goda Koshiro , Okazaki Renji , Akiba Kin-ya , Inamoto Naoki

… (X, Y=O,S) with organolithiums and Grignard reagents afforded different types of products depending on the combination of X and Y. … When Y=O, the reagents (R3M) mainly attacked the phosphorus atom to give Ph2P(=X)R3 …

Bulletin of the Chemical Society of Japan 51(1), 260-264, 1978

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12

Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates. II. : The Effects of Structure of O, S-Dialkyl Dithiocarbonates, Catalysts and Solvents [in Japanese]

KAWATA TOSHINOBU , HARANO KAZUNOBU , TAGUCHI TANEZO

… O, S-Dialkyl dithiocarbonate(I)は熱分解によりChugaev反応をうけるが, それに塩化アルミニウム(AlCl_3)を加え二硫化炭素中で反応させると収率よくS, S-dialkyl dithiocarbonate(II)へ転位することを報告した.また一般のチオール酸エステルをエタノールアミンの存在下蒸留すると容易にメルカプタンが留出するというメルカプタン合成法も発表した.そしてこの2つの反応を組合せ …

Journal of the Pharmaceutical Society of Japan 96(7), 832-840, 1976-07-25

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13

STUDIES OF PYRIMIDINE DERIVATIVES : (XXVI) ON S-ALKOXYCARBONYLTHIAMINE [in Japanese]

TAKAMIZAWA Akira , HAMASHIMA Yoshio , SATO Hisao

… Data presented in the previous paper have demonstrated that in oral administration O, S-bis (ethoxycarbonyl) thiamine (DCET) showed higher blood thiamine levels for a longer time than thiamine hydrochloride. …

Vitamins 29(1), 26-30, 1964-01-25

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14

Studies on the Pyrimidine Derivatives. XXII. The Syntheses of New Thiamine Derivatives.

Takamizawa Akira , Hirai Kentaro , Hamashima Yoshio

… O-Chlorocarbonylthiamine (VI) thus prepared was converted into O-carbamoylthiamine and O-alkoxycarbonylthiamine. … The free bases of O-carbamoyl derivatives were assigned dihydrothiochrome structures (XV) and (XVI). … S-Carbamoylthiamine derivatives were also prepared. …

Chemical & pharmaceutical bulletin 11(7), 882-887, 1963-07-25

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15

Studies on the Pyrimidine Derivatives. XXI. On the Studies of S-Alkoxycarbonylthiamine. (2).

Takamizawa Akira , Hirai Kentaro , Hamashima Yoshio

… HCl decomposition of S-ethoxycarbonylthiamine (I) gave 2-methyl-4-amino-5-aminomethylpyrimidine (II), formic acid and 3-ethoxycarbonylthio-5-hydroxy-2-pentanone (III). … A part of it was decomposed into O-ethoxycarbonylthiamine (IV) and thiamine (V). … Also O, S-bis (ethoxycarbonyl) thiamine (IX) decomposed into (II), formic acid and 3-ethoxycarbonylthio-5-ethoxycarbonyl-2-pentanone (X) by heating with HCl. …

Chemical & pharmaceutical bulletin 10(11), 1107-1112, 1962-11-25

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