Solvomercuration-demercuration. 9. Oxymercuration-demercuration of chloro-, epoxy-, and thiomethyl-substituted alkenes

Brown, Herbert C.; Lynch, Gary J.

doi:10.1021/jo00318a019

Cited by 18 publications

(2 citation statements)

References 3 publications

(3 reference statements)

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“…GB/T20824-2007 中将 3-甲硫基丙醇规定为芝麻香型白酒的特征风味物质, 并限定高度数酒中 3-甲硫基丙醇质量浓度须大于 0.5 mg/L, 低度数酒质量浓度须大于 0.4 mg/L [13] (GB/T 20824-2007 芝麻香型白酒, 中国标准出版社, 北京, 2007). 主要合成方法是由相应的硫醇与 γ-羟基烷基卤化物 23 通过亲核取代反应合成得到(Scheme 3a) [14] . 也可以由相应的硫醇对 α,β-不饱和醛的 Michael 加成来合成(Scheme 3b) [15] .…”

Section: 硫醚类unclassified

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Wang¹,

Wang²,

Jiang³

2019

Chin. J. Org. Chem.

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Scientists have found more and more sulfur compounds in food with the development of science and technology, high-precision analytical methods and equipment. In 2015, Flavor and Extract Manufactures Association of the United State published 2816 safe flavors, and there are more than 388 sulfur-containing compounds, accounting for more than 13%. The main smell of sulfur-containing flavors is food, especially the non-staple food and dishes. It is mainly used as food flavor, flower flavor and fruity flavor. Due to the increase of sulfur-containing perfume and flavors demand, its production scale is increasing, the research on synthesis methods is also deepening, and the green and efficient construction methods are also constantly reported. In this review, the recent progress in the construction of sulfide, thiol, thioester and polysulfide perfume & flavors is summarized.

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Section: 硫醚类unclassified

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Wang¹,

Wang²,

Jiang³

2019

Chin. J. Org. Chem.

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“…In more detail, on the one hand, a Lewis acid catalyzed ring-opening of cyclic ethers with acid chlorides as nucleophiles has the advantage of providing a variety of chloroesters with easy tunable chain lengths, since a great number of ethers are commercially available. During the years various methods based on Lewis acids have been introduced for the ring opening of cyclic ethers [8][9][10][11][12][13][14][15][16][17][18][19][20]. Among those protocols the application of zinc-salts as catalysts is advantageously, because it is abundant, cheap and low toxic.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of δ- and ε-Cyanoesters by Zinc-Catalyzed Ring-Opening of Cyclic Ethers with Acid Chlorides and Subsequent Cyanation

Enthaler

Weidauer

2011

Catal Lett

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In the present study, the zinc-catalyzed cleavage of cyclic ethers with acid halides as nucleophiles to yield chloroesters with different chain length has been investigated in detail. In the presence of straightforward and commercially available zinc salts as pre-catalysts excellent yields and selectivities were feasible. After studying the reaction conditions and the scope of the method, several efforts were carried out to understand the reaction mechanism. The obtained chloroesters were subsequently converted to d-and e-cyano esters, which are useful precursors in natural product synthesis.

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Desaminierungsreaktionen, 41. Reaktionen aliphatischer Diazonium‐Ionen und Carbokationen mit Ethern

Kirmse

Jansen

1985

Chem. Ber.

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Aliphatische Diazonium-Ionen und Carbokationen wurden durch Entacylierung der entsprechenden Nitrosoharnstoffe (1,5,9) in AlkohoVEther-Gemischen oder in 2-Alkoxyethanolen erzeugt. Die Ether waren den Alkoholen beim Abfangen kationischer Zwischenstufen stets unterlegen. Die Bildung von Trialkyloxonium-Ionen fuhrte zu Alkylaustausch oder Ringaffnung. Die Reaktivitatsabstufungen n-Butyl > Isobutyl bei Diazonium-Ionen, Ally1 > sec-Butyl > tert-Butyl bei Carbokationen, Methoxy > Ethoxy und Oxiran > Oxetan > Tetrahydrofuran bei Ethern weisen auf das Vorherrschen sterischer Effekte hin. Nachbargruppenbeteiligung war bei 4-Methoxy-1-butandiazonium-Ionen (58) und 4,5-Epoxy-l-pentandiazonium-Ionen (74) nachweisbar, aber wenig effektiv (< 20% cyclische Oxonium-Ionen). Deamination Reactions, 41 1) Reactions of Aliphatic Diazonium Ions and Carbocations with EthersAliphatic diazonium ions and carbocations were generated by deacylation of appropriate nitrosoureas (1,5,9) in alcohol-ether mixtures or in 2-alkoxyethanols. Ethers were generally inferior to alcohols in capturing cationic intermediates. Formation of trialkyloxonium ions led to alkyl exchange or ring opening. The observed reactivity orders were n-butyl > isobutyl for the diazonium ions, ally1 > sec-butyl > tert-butyl for the carbocations, methoxy > ethoxy and oxirane > oxetane > tetrahydro furan for the ethers, indicating the predominance of steric effects.Neighboring group participation in 4-methoxy-1-butanediazonium ions (58) and 4J-epoxy-l-pentanediazonium ions (74) was detectable but inefficient (< 20% of cyclic oxonium ions).

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Solvomercuration-demercuration. 9. Oxymercuration-demercuration of chloro-, epoxy-, and thiomethyl-substituted alkenes

Cited by 18 publications

References 3 publications

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Synthesis of δ- and ε-Cyanoesters by Zinc-Catalyzed Ring-Opening of Cyclic Ethers with Acid Chlorides and Subsequent Cyanation

Desaminierungsreaktionen, 41. Reaktionen aliphatischer Diazonium‐Ionen und Carbokationen mit Ethern

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