THIOCARBONYLS. IV. THE STRUCTURE OF DIFLUORYL TRISULFIDE AND DIBENZOPHENONE TRISULFIDE<sup>1</sup>

Campaigne, E.; Reid, Wm. Bradley

doi:10.1021/jo01170a012

Cited by 17 publications

(6 citation statements)

References 10 publications

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“…The cyclic trisulfide below is obtained by passing dry air through thiobenzophenone. Its structure is proved by chlorination to benzophenone dichloride, and by Raney nickel desulfuration to diphenylmethane (89). Heating regenerates thiobenzophenone (390).…”

Section: A Alkyl and Aralkyl Disulfidesmentioning

confidence: 99%

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Tarbell¹,

Harnish²

1951

Chem. Rev.

153

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Section: A Alkyl and Aralkyl Disulfidesmentioning

confidence: 99%

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Tarbell¹,

Harnish²

1951

Chem. Rev.

153

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“…As mentioned in the introduction, the oldest method for the synthesis of 3,3,5,5‐tetraaryl‐1,2,4‐trithiolanes is the air‐oxygen‐mediated conversion of the corresponding aromatic thioketones, which is applicable only for the symmetrically substituted derivatives . This approach is still of preparative value.…”

Section: Methods For the Preparation Of 124‐trithiolanesmentioning

confidence: 99%

“…The correctness of the postulated structure was proved by treatment of 1b with Raney‐Ni, which led to diphenylmethane ( 3a ) as the sole product. An analogous structure 1c was attributed to the product obtained after mild oxidation of thiofluorenone ( 2b ) (Scheme ).…”

Section: Introductionmentioning

confidence: 94%

Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

et al. 2019

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The review is aimed in summarizing the most important aspects of the chemistry of 1,2,4‐trithiolanes, which form a relevant class of cyclic polysulfides abundant in nature. Some of them were identified as components of Lenthinus edodes (shiitaki mushrooms) extracts as well as of Parkia speciosa (stink bean), which are well known in Asian cuisine. In addition, they determine the flavor of boiled beef and roasted chicken. Thermal decomposition of 1,2,4‐trithiolanes, either in solution or in the gas phase, results in [3+2]‐cycloelimination leading to the release of reactive thiocarbonyl S‐sulfides existing in equilibrium with sulfur‐rich, three‐membered dithiiranes. Both, 1,2,4‐trithiolanes and the products of their decomposition react with low‐valent platinum and iron compounds forming the corresponding sulfur‐metal complexes. For example, iron‐sulfur clusters formed in these reactions are of interest as structural models of [Fe,Fe]‐hydrogenase mimics.

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“…-Rf(Et20) = 0.57. -MS: m/z (%) = 361 (<I), 353 (3), 351 (9, 309 (l), 307 (2), 305 (2), 303 (6) [M ' ' -57; "~l ] , 289 (l), 287 (3), 249 (18), 247 (56), 205 (12), 203 (36), 183 (7), 134 (8), 111 (8), 98 (7), 57 (100). Following General Procedure 5, crude 12d in 20 ml of CHzCl2 in the presence of 5 ml (65 mmol) of TI'A was deprotected after ca.…”

mentioning

confidence: 99%

“…The spectral data were in agreement with that already reported"'"'. For the char--441,74 (37), 57(63) 56. (100).…”

mentioning

confidence: 99%

Synthesis of Nonproteinogenic (R)‐ or (S)‐Amino Acids Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert‐Butyl 2‐(tert‐Butyl)‐3‐methyl‐4‐oxo‐1‐imidazolidinecarboxylate (Boc‐BMI)

Seebàch¹,

Dziadulewicz²,

Behrendt³

et al. 1989

Liebigs Ann. Chem.

119

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The enantiomerically pure glycine derivatives (R)‐ and (S)‐Boc‐BMI, commercially available on a kg scale, are used as starting materials (Scheme 1) for the preparation of (i) open‐chain amino acids such as α‐deuterio amino acids (4, 5), β‐arylalanines (2), aspartic acid derivatives (6, 7a, 8), or ω‐halo amino acids (7b, c, 12, 13, 16, 17, 19, 22), (ii) of α‐aminocycloalkanecarboxylic acids (9, 11), and (iii) of heterocyclic α‐amino acids (14, 15, 18, 20) containing azetidine, pyrrolidine, piperidine or perhydroazepine rings. Inversion by deprotonation / protonation or deuteration allows to prepare either enantiomer of an amino acid from the same Boc‐BMI enantiomer (Scheme 5). Effects of additives such as the cyclic urea DMPU, lithium salts, or secondary amines upon the reactivity of lithium enolates are discussed and, in part, exploited.

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THIOCARBONYLS. IV. THE STRUCTURE OF DIFLUORYL TRISULFIDE AND DIBENZOPHENONE TRISULFIDE¹

Cited by 17 publications

References 10 publications

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

Synthesis of Nonproteinogenic (R)‐ or (S)‐Amino Acids Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert‐Butyl 2‐(tert‐Butyl)‐3‐methyl‐4‐oxo‐1‐imidazolidinecarboxylate (Boc‐BMI)

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THIOCARBONYLS. IV. THE STRUCTURE OF DIFLUORYL TRISULFIDE AND DIBENZOPHENONE TRISULFIDE1

Cited by 17 publications

References 10 publications

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

Organic and Coordination Chemistry of 1,2,4‐Trithiolanes

Synthesis of Nonproteinogenic (R)‐ or (S)‐Amino Acids Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert‐Butyl 2‐(tert‐Butyl)‐3‐methyl‐4‐oxo‐1‐imidazolidinecarboxylate (Boc‐BMI)

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THIOCARBONYLS. IV. THE STRUCTURE OF DIFLUORYL TRISULFIDE AND DIBENZOPHENONE TRISULFIDE¹