CiNii Articles - Alkenyl sulfoxide

1

Annulative Synthesis of Benzofurans from General Alkenyl Sulfoxides and Phenols via Pummerer/Sigmatropic Cascade

Hori Mitsuki , Yanagi Tomoyuki , Murakami Kei , Nogi Keisuke , Yorimitsu Hideki

… In addition to ketene dithioacetal monoxides that were specially designed and have been used so far, general alkenyl sulfoxides of moderate reactivity have now become applicable as substrates in the trifluoroacetic anhydride-mediated annulation with phenols for the shorter-step and transition-metal-free synthesis of benzofurans having diverse substituents. …

Bulletin of the Chemical Society of Japan 92(2), 302-311, 2019

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2

Exploitation of the Chemistry of Magnesium Carbenoids and Their Use in Organic Synthesis [in Japanese]

SATOH Tsuyoshi

… In order to solve the problem mentioned above, we used α-haloalkyl (or alkenyl) aryl sulfoxides as the precursors and used sulfoxide-magnesium exchange reaction for generation of much mild magnesium carbenoids. … α-Haloalkyl (or alkenyl) aryl sulfoxides are quite easily synthesized in high overall yields. …

YAKUGAKU ZASSHI 129(9), 1013-1023, 2009

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3

A New Method for Generation of Magnesium Carbenoids and Magnesium Carbanions, and its Application to Organic Synthesis [in Japanese]

SATOH Tsuyoshi

… This reaction is called sulfoxide-metal exchange reaction. …

Journal of Synthetic Organic Chemistry, Japan 61(2), 98-110, 2003-02-01

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4

Homo-Coupling Reactions of Alkenyl- and Arylfluorosilanes Mediated by a Copper(I) Salt

Nishihara Yasushi , Ikegashira Kazutaka , Toriyama Fumihiko , Mori Atsunori , Hiyama Tamejiro

… Homo-coupling reactions of an alkenyl- or arylsilane readily occur with a copper(I) salt in an aprotic polar solvent such as N, N-dimethylformamide or dimethyl sulfoxide under an aerobic condition to give the corresponding conjugated dienes or biaryls, respectively. …

Bulletin of the Chemical Society of Japan 73(4), 985-990, 2000

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5

Synthesis of Alkenyl-and Aryldifluoroacetate Using a Copper Complex from Ethyl Bromodifluoroacetate

SATO Kazuyuki , KAWATA Ryuichi , AMA Fumitaka , OMOTE Masaaki , ANDO Akira , KUMADAKI Itsumaro

… Ethyl bromodifluoroacetate reacted with alkenyl or aryl iodides in the presence of copper powder in dimethyl sulfoxide (DMSO) to give the corresponding alkynyl- or aryldiffuoroacetates in moderated to good yields. …

Chemical and Pharmaceutical Bulletin 47(7), 1013-1016, 1999-07-15

References (16) Cited by (1)
6

Synthesis of Alkenyl- and Aryldifluoroacetate Using a Copper Complex from Ethyl Bromodifluoroacetate.

SATO Kazuyuki , KAWATA Ryuichi , AMA Fumitaka , OMOTE Masaaki , ANDO Akira , KUMADAKI Itsumaro

… Ethyl bromodifluoroacetate reacted with alkenyl or aryl iodides in the presence of copper powder in dimethyl sulfoxide (DMSO) to give the corresponding alkynyl- or aryldiffuoroacetates in moderated to good yields. …

Chemical and Pharmaceutical Bulletin 47(7), 1013-1016, 1999

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7

A New Development in Organic Synthesis with Sulfoxides: Novel Synthetic Methods through the Ligand Exchange Reaction of Sulfoxides [in Japanese]

SATOH Tsuyoshi

… 1) the discovery of the ligand exchange reaction of sulfoxides, 2) S-aryl bond-cleavage via the ligand exchange, 3) S-alkenyl bond-cleavage via the ligand exchange, 4) S-alkyl bond-cleavage via the ligand exchange and new synthetic methods, 5) generation of carbenoids via the ligand exchange and new synthetic methods, 6) overview. …

Journal of Synthetic Organic Chemistry, Japan 54(6), 481-489, 1996-06-01

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8

Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt.

TAKEMOTO Yoshiji , TAKEUCHI Jun , OHRA Taiichi , MAEZAKI Naoyoshi , TANAKA Tetsuaki , IWATA Chuzo

… (6S, 7S)-1-Oxa-7-bromomethylspiro[5.5]undecanes (12 and 13) were synthesized from the optically active alkenyl sulfoxide (7). …

Chemical and Pharmaceutical Bulletin 41(11), 2034-2037, 1993

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9

Construction of Asymmetric Quaternary Carbon Center Containing Heteroatom via Regioselective Cleavage of Cyclopropane Ring Mediated by Mercury(II) Salt

TAKEMOTO Y. , TAKEUCHI Jun , OHRA Taiichi , MAEZAKI Naoyoshi , TANAKA Tetsuaki , IWATA Chuzo

… (6S, 7S)-1-Oxa-7-bromomethylspiro[5.5]undecanes (12 and 13) were synthesized from the optically active alkenyl sulfoxide (7). …

Chem. Pharm. Bull. 41, 2034-2037, 1993

Cited by (3)
10

22 SYNTHESIS OF TERPENOID DIALDEHYDES [in Japanese]

Isoe S. , Takemoto T. , Inaba H. , Han Q. , Nakatani K. , Katsumura S. , Yamamoto K. , Fujiwara S. , Hori K.

… Optically active key intermediate was synthesized from natural geniposide in high yield by the sequence involving Evans rearrangement of allyl phenyl sulfoxide derivative. … Manoalide and seco-manoalide were synthesized from methyl 7,8-dihydro-β-ionylidene acetate in high yield by the new method utilizing regioselective singlet oxygen oxidation of 3-alkenyl-5-trimethylsilyl furan to β-alkenyl-γ-hydroxybutenolide. …

Symposium on the Chemistry of Natural Products, symposium papers 27(0), 160-167, 1985

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11

A dimethyl sulfoxide-mediated oxidation of arylalkyl and alkyl alcohols to corresponding aldehydes and ketones via tropolonyl ethers.

Takeshita Hitoshi , Mametsuka Hiroaki , Matsuo Norihide

… The arylmethyl and diarylmethyl ethers of tropolones were oxidized to the corresponding carbonyl derivatives by heating in dimethyl sulfoxide. … This oxidation was applicable to alkyl ethers, but not to alkenyl ethers, which are known to cause the Claisen-rearrangement. …

Bulletin of the Chemical Society of Japan 55(4), 1137-1139, 1982

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12

The Structure-Activity Relationships of Antibacterial L-5-Alkylthiomethylhydantoin S-Oxides and Related Compounds:Hydantoin Derivatives of S-Alkyl-and Alkenyl-L-cysteine-S-oxides (Part II)

MIURA Yuzo , TAHARA Satoshi , MIZUTANI Junya

抗菌 (とくに抗細菌) 活性を有する L-5-alkylthiomethylhydantoin S-oxides および調製した関連化合物を用いて構造-活性の関係を調べた. ヒダントイン環をもたない S-propyl-L-cysteine-S-oxide, その< …

Journal of Pesticide Science 4(1), 25-28, 1979

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13

Synthesis of Antimicrobial L-5-Alkylthiomethylhydantoin S-Oxides and Related Compounds

MIZUTANI Junya , MIURA Yuzo , TAHARA Satoshi

… 10種類のL-5-alkyl-および alkenylthiomethylhydatoin S-oxides (alkyl または alkenyl: methyl, ethyl, propyl, isopropyl, allyl, butyl, isobutyl, sec-butyl, pentyl および hexyl), ならび関連化合物を調製した. …

Journal of Pesticide Science 4(1), 17-23, 1979

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14

1-Arylsulfinyl-1-alken-1-yllithium.

Okamura Hisashi , Mitsuhira Yoshiyuki , Miura Morikazu , Takei Hisashi

… The generation of the title compound (2) by the treatment of alkenyl aryl sulfoxide (1) with lithium diisopropylamide (LDA), and the reactions of 2 …

Chemistry Letters 7(5), 517-520, 1978

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15

Rearrangement and trans-Elimination Contrary to the Chugaev Reaction Rule. XI. Pyrolysis of Sodium 2-Alkenyl Xanthogenate [in Japanese]

HARANO KAZUNOBU , TAGUCHI TANEZO

… it was concluded that sodium 2-alkenyl trithiocarbonate, the precursor of di(2-alkenyl) and 2-alkenyl alkyltrithiocarbonates, might be formed by the following routes : Sodium 2-alkenyl dithiolcarbonate was formed by thermal rearrangement of sodium 2-alkenyl xanthogenate and then decomposed into sodium 2-alkenyl sulfide which reacted with carbon disulfide to give sodium 2-alkenyl trithiocarbonate. …

Journal of the Pharmaceutical Society of Japan 93(6), 804-810, 1973-06

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16

Rearrangement and trans-Elimination Contrary to the Chugaev Reaction Rule. XI. Pyrolysis of Sodium 2-Alkenyl Xanthogenate

HARANO KAZUNOBU , TAGUCHI TANEZO

… it was concluded that sodium 2-alkenyl trithiocarbonate, the precursor of di(2-alkenyl) and 2-alkenyl alkyltrithiocarbonates, might be formed by the following routes : Sodium 2-alkenyl dithiolcarbonate was formed by thermal rearrangement of sodium 2-alkenyl xanthogenate and then decomposed into sodium 2-alkenyl sulfide which reacted with carbon disulfide to give sodium 2-alkenyl trithiocarbonate. …

YAKUGAKU ZASSHI 93(6), 804-810, 1973

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