Organomercury Compounds in Organic Synthesis

Larock, Richard C.

doi:10.1007/978-3-642-70004-0

Cited by 103 publications

(61 citation statements)

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“…Reactions of 1 with arylaldehyde and 1,5-diphenylthiocarbazone (dptc) were thoroughly investigated and, indeed, the structure of a (E)-acetyloxy Table 1 Crystal data and refinement details for compounds [1] Table 4 Selected bond lengths (Å) and angles (º) for [3] obtained by excitation at the respective absorption maxima (refer to Table 2). Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 1 was prepared from aniline and mercury(II) acetate according to published method [3] with some modification. To an aqueous suspension of Hg(OAc) 2 (5.0 g, 15.688 mmol) in 25 mL of water, 2.9 mL (2.96 g, 31.783 mmol) of freshly distilled aniline was added under stirring conditions, whereupon a clear solution was formed initially followed by the rapid formation of a white precipitate.…”

Section: Synthesis Of Acetyloxy(4-aminophenyl)mercury(ii) (1)mentioning

confidence: 99%

“…The early development of organomercurial chemistry as compared to other organometallic compounds can be attributed to the high stability of organomercury compounds to air and moisture. Despite high toxicity, organomercury compounds accommodate all functional groups and their remarkable chemical and thermal stability have made them particularly attractive as synthetic intermediates [3].…”

Section: Introductionmentioning

confidence: 99%

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An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Baul

Longkumer

Linden

2014

Journal of Organometallic Chemistry

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A series of pale yellow imine-functionalized acetyloxy(4-(arylideneamino)phenyl)mercury(II) compounds (2-7) were obtained by the reactions of acetyloxy(4-aminophenyl)mercury(II) (1) with arylaldehydes in equimolar ratios in absolute ethanol under reflux conditions. Organomercury compounds 2-5 and 7, when treated with 1,5-diphenylthiocarbazone (dptc) in chloroform, formed dark-red (4-((E)-arylideneamino)phenyl)(((Z)-((E)-phenyldiazenyl) (2-phenylhydrazono)methyl)thio)mercury compounds (8e12) in alkaline medium. The reaction of 7 with a slight excess of mercuric chloride in anhydrous methanol led to the formation of the bimetallic compound (2-[4-(acetyloxymercuryl) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT[ Construction of mono-and a bi-metallic organomercury/mercury and organomercury/cadmium compounds were accomplished from an enzyme activator via suitably designed imine-functionalized organomercury ligand. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Acetyloxy(4-aminophenyl)mercury(ii) (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Baul

Longkumer

Linden

2014

Journal of Organometallic Chemistry

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“…For more lipophilic compounds (e.g. phenyl fatty acids) an ethanol/water mixture of 7/3 (vv) proved useful [60,63]. For basic lipophilic compounds an aqueous solution of <10% acetic acid avoids side products.…”

Section: Cu(i)-assisted Radioiodinationmentioning

confidence: 99%

Radioionidation Reactions for Radio Pharmaceuticals

Coenen¹,

Mertens²,

Mazieère³

2006

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HB) ISBN-13 978-1-4020-4560-8 (HB) ISBN-10 1-4020-4561-1 (e-book) Published by Springer, All rights reserved. ß 2006 Springer No part of this work may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission from the Publisher, with the exception of any material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work.Printed in the Netherlands. PREFACEFounded in 1971, COST is an intergovernmental framework for European Cooperation in the field of scientific and technical research, allowing the coordination of nationally funded research on a European level. COST actions cover basic and precompetitive research, as well as activities of public utility. The goal of COST is to ensure that Europe holds a strong position in the field of scientific and technical research for peaceful purposes, by increasing European cooperation and interaction.COST consists in actions, the duration of which is generally 4 years. Two actions, COST B3 entitled ''Development of New Radiotracers and Methods of Quality Assurance for Nuclear Medicine Applications'' and COST B12 entitled ''Radiotracers for In Vivo Assessment of Biological Functions'', which have been devoted to radiopharmaceutical chemistry and radiopharmaceutical validation, were successfully completed.Radiochemical methodology constitutes the most important base for successful in vivo functional imaging in nuclear medicine. For single-photon emission tomography (SPET) imaging, radioiodination methodology allows the development of potent radiotracers, and several of them are presently in clinical routine.Many previous publications have tackled the specific problems of radioiodination, but the time for a state-of-the-art book seemed right now since this field has advanced over the last 30 years to reach a level where guidelines and expert systems can be suggested for the main methodological aspects. This book has emerged from an original idea during the course of COST Action B3 and was developed during the course of COST Action B12 with the help of many recognised European experts in the field. Sincere thanks to all of them for their very precious support, advice and contributions.The authors gratefully acknowledge the support of COST, which, all along the duration of the actions, has encouraged the preparation and the finalisation of a collective textbook.

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“…Um método para a construção de compostos α-diazo carbonilados que tem recebido especial atenção envolve modificações químicas com retenção da função diazo, particularmente via reações de metalação 7,[9][10][11][12][13][14][15] . Por exemplo, a preparação de uma grande variedade de α-diazo-β-cetoésteres 1 pode ser convenientemente efetuada, a partir da reação entre o mercurial diazo éster 2 16,17 e haletos de ácidos, em condições essencialmente neutras (Esquema 1) 18 .…”

Section: Figuraunclassified

Reações de inserção intramolecular de diazo compostos polifuncionais catalisadas por ródio(II): síntese de oxetan-3-ona-2-carboxilato e outros heterociclos funcionalizados

Padwa¹,

Sá²

1999

Quím. Nova

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Recebido em 4/1/99; aceito em 31/3/99 RHODIUM(II)-CATALYSED INTRAMOLECULAR INSERTION REACTION OF MULTIFUNC-TIONAL DIAZO COMPOUNDS: SYNTHESIS OF OXETAN-3-ONE-2-CARBOXILATE AND OTHER HETEROCYCLES.γ-Hydroxy-α-diazo-β-ketoesters are key intermediates in the chemistry of penicilin-based antibiotics and natural products. The method developed here for the synthesis of ethyl 2-diazo-4-hydroxy-3-oxo-butanoate 17 (in two steps from the diazo mercurial 2) compares very favorably with those reported in the literature for similar compounds. The Rh 2 (OAc) 4 -mediated intramolecular OH-insertion reaction of the diazo hydroxy ester 17 was investigated, furnishing the oxetan-3-one-2-carboxilate 18 in good yield. When the diazo ester lacks a free hydroxyl group as in the case of the phenoxy diazo ester 11 an intramolecular CH-insertion takes place, affording the 2H-chromene 20 in almost quantitative yield. The behavior of other functionalized diazo esters towards Rh 2 (OAc) 4 was also investigated.Keywords: diazoesters; intramolecular insertion reaction; rhodium carbenoid. ARTIGO INTRODUÇÃOA utilização de compostos α-diazo carbonilados em síntese orgânica tem se apresentado como um excelente método na preparação de sistemas estruturalmente complexos, como heterociclos e produtos naturais. A razão para isso reside no fato de que compostos α-diazo carbonilados participam em uma grande variedade de transformações químicas, incluindo ciclopropanação, rearranjo de Wolff, dimerização, α,α-substituição, X-H inserção (X= C, O, N, S), cicloadição, formação de ilídeos, etc. Todos esses processos podem ocorrer tanto inter como intramolecularmente, através da eliminação de nitrogê-nio molecular [1][2][3][4][5][6][7] . A recente descoberta de que metais de transição (especialmente ródio(II)) catalisam a eliminação de N 2 em compostos α-diazo carbonilados promovendo a formação de metalocarbenóides como intermediários reativos fez aumentar ainda mais o interesse em sistemas contendo um grupo diazo (Figura 1) [1][2][3][4][5] . A exploração sintética destes fenômenos (particularmente em reações de ciclopropanação, inserção e cicloadições) está intimamente associada aos estudos mecanísticos envolvendo o comportamento dos metais de transição no processo catalítico e na geração das espécies reativas. Uma grande variedade de heterociclos é obtida a partir de reações de inserção de diazo compostos catalisada por ródio(II) (Equação 1). Já a presença de um grupo carbonilado δ Endereço atual para correspondência: Departamento de Química, Universidade Federal de Santa Catarina, Campus de Trindade, 88040-900, Florianópolis, SC e-mail: msa@qmc.ufsc.br adequadamente distante da função diazo permite a formação de ilídeos reativos, participantes em reações de cicloadição 1,3 dipolar gerando oxabiciclos (Equação 2) 1-5 . Figura 1O desenvolvimento de metodologias eficientes na preparação de compostos α-diazo carbonilados tem permitido o acesso cada vez maior a estes sistemas [5][6][7][8][9] . Um método para a construção de compostos α-diazo carbonilados que tem...

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Organomercury Compounds in Organic Synthesis

Cited by 103 publications

References 11 publications

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Radioionidation Reactions for Radio Pharmaceuticals

Reações de inserção intramolecular de diazo compostos polifuncionais catalisadas por ródio(II): síntese de oxetan-3-ona-2-carboxilato e outros heterociclos funcionalizados

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