Electrophilic thallation of phenol and its derivatives with phenylthallium(III) crown ether complexes

Kakiuchi, Fumitoshi; Kawasaki, Yoshikane.; Enomoto, Norihide.; Akita, Hiroshi; Ohe, Kouichi; Chatani, Naoto; Murai, Shinji

doi:10.1021/om00052a063

Cited by 5 publications

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“…The AMI geometries and charges for the germanium analogs of propane (1), cyclopropane (2), and cyclobutane (3) are listed in Table I. There are no experimental results available on the structure of 1.…”

Section: Resultsmentioning

confidence: 99%

“…The AMI distance is also shorter than that predicted by ab initio calculations for unsubstituted 2 (2.50 Á).8 AMI also underestimates the Ge-Ge A more serious problem becomes evident when the calculated atomic charges on the germanium atoms are compared. The cyclopropane analog (2) contains chemically equivalent germanium atoms. As would be predicted a priori from the modest electronegativity difference between germanium and hydrogen, the calculated charges on the germanium atoms are small.…”

Section: Resultsmentioning

confidence: 99%

“…We wish to report here a more detailed analysis of the origin of this problem based on examination of the AMI parameter values. To this end, we have examined the results of AMI calculations on trigermapropane (germanapropane, Ge3H8, 1), trigermacyclopropane (germanacyclopropane, Ge3H6, 2), and tetragermacyclobutane (germanacyclobutane, Ge4H8, 3).…”

Section: Introductionmentioning

confidence: 99%

“…AMI Geometries and Atomic Charges for Germanapropane (1), Germanacyclopropane (2), and Germanacyclobutane(3) …”

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confidence: 99%

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Cautions on use of the AM1 semiempirical parameters for germanium

Holder¹,

Earley²

1992

Organometallics

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Reaction of Lithium 2,3,4,5-Tetramethylpyrrolide with [(i)4-C7H8)RuCl2],. In a three-necked round-bottom flask, equipped with a bar stirrer, nitrogen inlet, and septum, was added 2,3,4,5-tetramethylpyrrole (1.23 g, 10.0 mmol) and dry tetrahydrofuran (70 mL). To the stirred solution under nitrogen was added 6.9 mL (11.0 mmol) of a 1.6 M solution of n-butyllithium in hexane. The solution was stirred under nitrogen for 1 h, [(7j4-C7H8)RuCl2], (1.31 g 5.0 mmol) was added, and the mixture was stirred for 15 h. The solvent was evaporaed under a steady stream of dry nitrogen to give a black solid, which was extracted with two 100-mL portions of pentane. The volume of pentane was reduced under a stream of nitrogen to a volume of 5 mL and chromatographed on a 15-cm column of activity III neutral alumina. Elution with chloroform-acetone (1:1) gave a light brown solid, which was recrystallized from pentane to give 1.37 g (78% yield) of 2 as orange-brown crystals. The complex was identified as above.Acknowledgment. The helpful comments of Professor C. H. Winter are greatly appreciated.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…AMI Geometries and Atomic Charges for Germanapropane (1), Germanacyclopropane (2), and Germanacyclobutane(3) …”

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