Lead tetraacetate and pyridine. New, mild conditions for a Hofmann-like rearrangement. New synthesis of 2-oxazolidinones

S. Stoney Simons

doi:10.1021/jo00943a002

Lead tetraacetate and pyridine. New, mild conditions for a Hofmann-like rearrangement. New synthesis of 2-oxazolidinones

The Journal of Organic Chemistry ◽

10.1021/jo00943a002 ◽

1973 ◽

Vol 38 (3) ◽

pp. 414-416 ◽

Cited By ~ 20

Author(s):

S. Stoney Simons

Keyword(s):

Lead Tetraacetate ◽

Mild Conditions ◽

New Synthesis

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An Efficient New Synthesis of Racemic Cetiedil and a Novel Route to α-Ketocarboxylic Acids Utilising Mild Conditions

Synlett ◽

10.1055/s-2007-977414 ◽

2007 ◽

Vol 2007 (08) ◽

pp. 1211-1214 ◽

Cited By ~ 3

Author(s):

Craig Roxburgh ◽

C. Ganellin ◽

Andrew Thorpe

Keyword(s):

Mild Conditions ◽

New Synthesis

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Reaction of Trialkylboranes with Cyclic α-Diazo Ketones. A New Synthesis of α-Alkyl Cycloalkanones

Canadian Journal of Chemistry ◽

10.1139/v71-385 ◽

1971 ◽

Vol 49 (13) ◽

pp. 2371-2373 ◽

Cited By ~ 13

Author(s):

John Hooz ◽

Donald M. Gunn ◽

Hiromichi Kono

Keyword(s):

Cyclic Ketones ◽

Efficient Procedure ◽

Mild Conditions ◽

New Synthesis ◽

Reaction Proceeds ◽

High Yields

An efficient procedure has been developed for the alkylation of cyclic ketones, based on the reaction of trialkylboranes with cyclic α-diazo ketones. The reaction proceeds under mild conditions, affords high yields of α-alkylated cycloalkanones, and circumvents certain difficulties inherent in previous alkylation methods.

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Diaryloxycarbenes from oxadiazolines

Canadian Journal of Chemistry ◽

10.1139/v01-016 ◽

2001 ◽

Vol 79 (3) ◽

pp. 319-327

Author(s):

Xiaosong Lu ◽

Darren L Reid ◽

John Warkentin

Keyword(s):

Acidic Solution ◽

Benzene Solution ◽

Subsequent Treatment ◽

Oxidative Cyclization ◽

Lead Tetraacetate ◽

Dimethyl Acetylenedicarboxylate ◽

Mild Conditions ◽

Product Mixture ◽

Carbonyl Ylide ◽

Ketene Acetal

Symmetric and unsymmetric 2,2-diaryloxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines were synthesized by oxidative cyclization of aryloxycarbonyl hydrazones of acetone with lead tetraacetate and subsequent treatment of the product mixture with a phenol in acidic solution. Thermolysis of the oxadiazolines in benzene solution at 110°C afforded carbonyl ylide intermediates that cyclize, in part, to the corresponding 2,2-diaryloxyoxirane intermediates. The oxiranes, which were not observed, are required to account for the 1,1-diaryloxy-2-methylpropenes (ketene acetals) that were isolated. Most of the carbonyl ylides fragment to acetone and diaryloxycarbenes. The latter form dimers (tetraaryloxyethenes) or they can be trapped with phenols to form orthoformates. Diphenoxycarbene was also trapped with dimethyl acetylenedicarboxylate (DMAD). The method appears to be the first for generating the parent diphenoxycarbene under relatively mild conditions in solution, and the only one to date for generating unsymmetrically substituted diaryloxycarbenes. Minor competing fragmentations of the oxadiazolines to 2-diazopropane and the appropriate diaryl carbonates, were also observed.Key words: diarylcarbonate, diaryloxycarbene, diaryloxy oxadiazoline, ketene acetal, orthoformate.

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Hydride-Induced Carbonylation of Trialkylboranes Followed by Treatment with Acid and Oxidation. A New Synthesis of Dialkylcarbinols under Mild Conditions

Synthesis ◽

10.1055/s-1978-24849 ◽

1978 ◽

Vol 1978 (09) ◽

pp. 676-677 ◽

Cited By ~ 19

Author(s):

John L.. HUBBARD ◽

Herbert C. BROWN

Keyword(s):

Mild Conditions ◽

New Synthesis

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Reactions of [2-(Bromomethyl)phenyl](4-chlorophenyl)methanone: A New Synthesis of [1,3]Thiazolo[3,2-b][2,4]benzodiazepine, Benzimidazo[1,2-b][2,4]benzodiazepine and Benzimidazo[1,2-b][2]benzazepine Derivatives

French-Ukrainian Journal of Chemistry ◽

10.17721/fujcv7i1p96-103 ◽

2019 ◽

Vol 7 (1) ◽

pp. 96-103

Author(s):

Lyudmyla M. Potikha ◽

Volodymyr V. Sypchenko ◽

Valentyn I. Davydov

Keyword(s):

Mass Spectrometry ◽

Elemental Analysis ◽

Nmr Spectra ◽

Quaternary Salt ◽

New Approach ◽

Mild Conditions ◽

New Synthesis ◽

Intramolecular Condensation ◽

Cyclic Compounds ◽

Azolium Salts

A new approach to the development of a number of azolo-condensed azepines and diazepines has been proposed. The method for the synthesis of [1,3]thiazolo[3,2-b][2,4]benzodiazepine, benzimidazo[1,2-b][2,4]benzodiazepineandbenzimidazo[1,2-b][2]benzazepinederivatives involves the reaction of [2-(bromomethyl)phenyl](4-chlorophenyl)methanonewith5-methyl-1,3-thiazol-2-amine, 1H-benzimidazol-2-amineand1,2-dimethyl-1H-benzimidazole. The formation of the quaternary salt of the initial diazole has been done under mild conditions in MeCN. The following intramolecular condensation has been realized by heating 2-amino azolium salts in AcOH or in Et3N as in the case of 2-methyl azolium salt. The structures of these cyclic compounds have been confirmed by mass spectrometry measurements, elemental analysis and NMR spectra.

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