OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES

A  PEREZENCABO; S  PERRIO; A M Z  SLAWIN; S E  THOMAS; A T  WIERZCHLEYSKI; D J  WILLIAMS

OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES

A PEREZENCABO, S PERRIO, A M Z SLAWIN, S E THOMAS, A T WIERZCHLEYSKI, D J WILLIAMS

Research output: Contribution to journal › Article › peer-review

Abstract

Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(o) complexes of alkylsulfinyl substituted arenes. The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl[eta6-1-methoxy-2-(methylsulfinyl)benzene]chromium(0) 20x, [eta6-1-(tert-butylsulfinyl)-2-methoxybenzene]tricarbonylchromium(o) 23x and tricarbonyl[eta6-1-(ethylsulfinyl)-2-methoxybenzene]chromium(o) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.

Original language	English
Pages (from-to)	629-642
Number of pages	14
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	6
Publication status	Published - 21 Mar 1994

Keywords

CHROMIUM-TRICARBONYL COMPLEXES
SULFINYL-CONTROLLED FORMATION
ASYMMETRIC-SYNTHESIS
ORGANIC-SYNTHESIS
STEREOSELECTIVE SYNTHESIS
ORGANOMETALLIC CHEMISTRY
ALDOL REACTION
DIMETHYLDIOXIRANE
SULFOXIDES
ARENE

Cite this

@article{996d266367dd4b6baf1ba6b6e31a0ced,

title = "OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES",

abstract = "Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(o) complexes of alkylsulfinyl substituted arenes. The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl[eta6-1-methoxy-2-(methylsulfinyl)benzene]chromium(0) 20x, [eta6-1-(tert-butylsulfinyl)-2-methoxybenzene]tricarbonylchromium(o) 23x and tricarbonyl[eta6-1-(ethylsulfinyl)-2-methoxybenzene]chromium(o) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.",

keywords = "CHROMIUM-TRICARBONYL COMPLEXES, SULFINYL-CONTROLLED FORMATION, ASYMMETRIC-SYNTHESIS, ORGANIC-SYNTHESIS, STEREOSELECTIVE SYNTHESIS, ORGANOMETALLIC CHEMISTRY, ALDOL REACTION, DIMETHYLDIOXIRANE, SULFOXIDES, ARENE",

author = "A PEREZENCABO and S PERRIO and SLAWIN, {A M Z} and THOMAS, {S E} and WIERZCHLEYSKI, {A T} and WILLIAMS, {D J}",

year = "1994",

month = mar,

day = "21",

language = "English",

pages = "629--642",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "6",

}

TY - JOUR

T1 - OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES

AU - PEREZENCABO, A

AU - PERRIO, S

AU - SLAWIN, A M Z

AU - THOMAS, S E

AU - WIERZCHLEYSKI, A T

AU - WILLIAMS, D J

PY - 1994/3/21

Y1 - 1994/3/21

N2 - Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(o) complexes of alkylsulfinyl substituted arenes. The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl[eta6-1-methoxy-2-(methylsulfinyl)benzene]chromium(0) 20x, [eta6-1-(tert-butylsulfinyl)-2-methoxybenzene]tricarbonylchromium(o) 23x and tricarbonyl[eta6-1-(ethylsulfinyl)-2-methoxybenzene]chromium(o) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.

AB - Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(o) complexes of alkylsulfinyl substituted arenes. The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl[eta6-1-methoxy-2-(methylsulfinyl)benzene]chromium(0) 20x, [eta6-1-(tert-butylsulfinyl)-2-methoxybenzene]tricarbonylchromium(o) 23x and tricarbonyl[eta6-1-(ethylsulfinyl)-2-methoxybenzene]chromium(o) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.

KW - CHROMIUM-TRICARBONYL COMPLEXES

KW - SULFINYL-CONTROLLED FORMATION

KW - ASYMMETRIC-SYNTHESIS

KW - ORGANIC-SYNTHESIS

KW - STEREOSELECTIVE SYNTHESIS

KW - ORGANOMETALLIC CHEMISTRY

KW - ALDOL REACTION

KW - DIMETHYLDIOXIRANE

KW - SULFOXIDES

KW - ARENE

M3 - Article

SN - 0300-922X

SP - 629

EP - 642

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 6

ER -

OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES

Abstract

Keywords

Fingerprint

Cite this