Oxidation of alkylthio substituted tricarbonyl(η<sup>6</sup>-arene)chromium(<scp>0</scp>) complexes to alkylsulfinyl substituted tricarbonyl(η<sup>6</sup>-arene)chromium(<scp>0</scp>) complexes

Pérez‐Encabo, Alfonso; Perrio, Stéphane; Slawin, Alexandra M. Z.; Thomas, Susan E.; Wierzchleyski, Adam T.; Williams, David J.

doi:10.1039/p19940000629

Cited by 22 publications

(7 citation statements)

References 53 publications

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“…This reaction confirms the ortho lithiation by the formation of 1-methoxy-2-(methylsulfanyl)benzene, which was identified from NMR spectroscopic data and GC MS data. [17,18] When the oxygen donor substituent of anisole is changed to the softer sulfur atom as in thioanisole, a similar result was expected. However, no CϪH bond activation was observed, instead NMR spectroscopic data indicated a cleavage of the SϪMe bond.…”

Section: Discussionsupporting

confidence: 74%

“…[9,10] As in previous co-condensations, a further confirmation of the regiochemistry was gained by the reaction of 2-methoxyphenyllithium with dimethyl disulfide. The observed product of this reaction was 1-methoxy-2-(methylsulfanyl)benzene in a quantitative yield, which was identified from NMR spectroscopic data and GC MS data [17,18] as shown in Scheme 3. When the sulfur donor thioanisole was used, a different reaction occurred, resulting in a cleavage of the CϪS bond instead of CϪH bond activation.…”

Section: Experimental Studymentioning

confidence: 95%

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Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

2003

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Lithium atoms were co‐condensed with +I‐substituted benzene derivatives like trimethyl(phenyl)silane and tert‐butylbenzene in the presence of THF at 77 K, which resulted in C−H bond activation, to produce the aryllithium compound as well as the coupling of the substituted phenyl radicals. Other +I‐substituted benzene derivatives like xylene and mesitylene failed to react with lithium atoms in the presence of THF. Oxygen and nitrogen donor substituted benzene derivatives (anisole, N,N‐dimethylaniline, and N,N‐dimethylbenzylamine) showed activation of the ortho C−H bond when co‐condensed with lithium atoms in the presence of THF. However, when thioanisole was co‐condensed with lithium atoms and THF, a C−S bond cleavage occurred instead. These results were interpreted with the aid of DFT calculations, which show π‐ and σ‐complexes between the lithium clusters and benzene derivatives as reactive intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Discussionsupporting

confidence: 74%

Section: Experimental Studymentioning

confidence: 95%

Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

2003

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“…The most reliable and reproducable procedure previously published is the epoxidation with dimethyldioxirane. [21,29] Accordingly, the treatment of cryptophycin D (4) with dimethydioxirane [47] at Ϫ30°C for 2 h and room temperature for 10 h furnished cryptophycin B (2) in 87% yield as a 3:1 mixture of diastereomers (determined by 1 H NMR) (Scheme 4). Since both isomers could not be separated by flash column chromatography, clean separation of the major epoxide was accomplished by reversed phase HPLC (YMC-PACK OD-AQ 5S 120Å 4.6 ϫ 250 mm, MeOH/H 2 O, 3:1, 1 mL/ min).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Syntheses of Potent Antitumor Macrolides Cryptophycin B and Arenastatin A

Ghosh¹,

Bischoff²

2004

Eur J Org Chem

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“…The differences observed for the non-complexed compounds between the [5,6]chromene series (1, 2 and 3) and the [7,8]chromene series (4, 5 and 6) were still present after complexation (1b, 2b, 3b and 4b, 5b, 6b).…”

Section: Spectrokinetic Studies Of Complexesmentioning

confidence: 93%

Synthesis and photochromic properties of tricarbonylchromium complexes of 2H-?6-benzochromenes

Hannesschlager

Brun

2000

Appl. Organometal. Chem.

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Although in the 2H-chromene (benzopyran) series complexation with tricarbonylchromium, under thermal conditions, is totally regioselective, in the naphthopyran series the same reaction cannot be observed. We show here that with tricarbonyl(trispyridine)chromium as complexing agent, in the presence of Lewis acid, complexation of naphthopyrans can be achieved and is totally regioselective. The complexes formed are photochromic compounds, and their thermal bleaching kinetic constants are reduced as compared with the non-complexed homologous compound.

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Oxidation of alkylthio substituted tricarbonyl(η⁶-arene)chromium(0) complexes to alkylsulfinyl substituted tricarbonyl(η⁶-arene)chromium(0) complexes

Cited by 22 publications

References 53 publications

Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

Asymmetric Syntheses of Potent Antitumor Macrolides Cryptophycin B and Arenastatin A

Synthesis and photochromic properties of tricarbonylchromium complexes of 2H-?6-benzochromenes

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Oxidation of alkylthio substituted tricarbonyl(η6-arene)chromium(0) complexes to alkylsulfinyl substituted tricarbonyl(η6-arene)chromium(0) complexes

Cited by 22 publications

References 53 publications

Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

Co‐Condensation Reactions of Substituted Aromatic Compounds with Lithium Atoms at 77 K

Asymmetric Syntheses of Potent Antitumor Macrolides Cryptophycin B and Arenastatin A

Synthesis and photochromic properties of tricarbonylchromium complexes of 2H-?6-benzochromenes

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Oxidation of alkylthio substituted tricarbonyl(η⁶-arene)chromium(0) complexes to alkylsulfinyl substituted tricarbonyl(η⁶-arene)chromium(0) complexes