2,2',2″-Tripyrrylmethenes<sup>1,2</sup>

Castro, Albert J.; Corwin, Alsoph H.; Deck, J. F.; Wei, Pan

doi:10.1021/jo01092a013

Cited by 11 publications

(7 citation statements)

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“…Several works have appeared in the literature on the kinetics of the nucleophilic reactions of O-aryl S-aryl thio and dithiocarbonates. [1][2][3][4][5][6] Among these studies are the reactions of secondary alicyclic amines and pyridines with O-aryl S-(4-nitrophenyl) thiocarbonates, [3] and O-aryl S-(4-nitrophenyl) dithiocarbonates, [4,5] where there are two possible nucleofuges of different nature (benzenethiolates versus phenoxides). The question is which of the groups is the nucleofuge.…”

Section: Introductionmentioning

confidence: 99%

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

Castro

Aliaga

Gazitúa

et al. 2012

J of Physical Organic Chem

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A kinetic investigation is undertaken on the pyridinolysis of S‐phenyl O‐(4‐nitrophenyl) dithiocarbonate (1), S‐(4‐nitrophenyl) O‐(4‐nitrophenyl) dithiocarbonate (2) and S‐phenyl O‐(4‐nitrophenyl) thiocarbonate (3) in aqueous ethanol. The Brønsted‐type plots (log kN versus pKa) obtained are linear and are explained by a stepwise mechanism with the existence of a tetrahedral intermediate (T±) and its breakdown to products as the rate determining step. The high‐performance liquid chromatography analysis of the products of these reactions and that for the reaction of S‐(4‐chlorophenyl) O‐(4‐nitrophenyl) dithiocarbonate (4) with 4‐oxypyridine shows that 4‐nitrophenoxide is the principal (or the sole) leaving group in these reactions. From the results obtained in the reaction of compound 2, it can be concluded that 4‐nitrophenoxide is a better nucleofuge than 4‐nitrobenzenethiolate from the same tetrahedral intermediate, although the former is three pKa units more basic than the latter. Reasons for this behaviour are given. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

Castro

Aliaga

Gazitúa

et al. 2012

J of Physical Organic Chem

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“…Form ation o f the red pigm ent (1) T he fo rm atio n o f th e red pig m en t (1) (see Fig. 1) is not grow th associated w hich is characteristic for a secondary m etabolite.…”

Section: R Esults and Discussionmentioning

confidence: 99%

“…O ften carotenoides, phenazine and pyrrole com pounds, as well as azaquinones and anthocyanes, are responsible for these findings. Among the red com pounds p roduced by bacteria prodigiosin from Serratia marcescens [1] and som e analogous substances such as undecylprodigiosin from Streptomyces longisporusruber [2,3] and a cyclic pigm ent from Alterom onas rubra [4] are well know n examples.…”

Section: Introductionmentioning

confidence: 99%

A New Red Dipyrromethene Pigment from Candida boidinii

Lang

Beyer

Sistig

et al. 1983

Zeitschrift Für Naturforschung C

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“…1, A) of WREDE and ROTHHAAS (1933b) has now been established as correct. TREIBS and HINTERMEIER (1957) and CASTRO et al (1959a) examined absorption spectra of several synthetic tripyrrylmethenes and concluded that comparison with the spectrum of prodigiosin did not support the original structure (Fig. 1, B) proposed by .…”

Section: Chemistrymentioning

confidence: 93%

Biosynthesis

1967

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All rights, especially that of translation into f oreign 1anguages, reserved. It is also forbidden to reproduce this book, either who1e or in part, by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written pennission from Springcr-Vcrlag Berlin Heide1bCig GmbH. DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this sUbject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The...

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2,2',2″-Tripyrrylmethenes^1,2

Cited by 11 publications

References 0 publications

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

A New Red Dipyrromethene Pigment from Candida boidinii

Biosynthesis

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2,2',2″-Tripyrrylmethenes1,2

Cited by 11 publications

References 0 publications

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

The nucleofuge in the pyridinolysis of O‐(4‐nitrophenyl) S‐aryl thio and dithiocarbonates

A New Red Dipyrromethene Pigment from Candida boidinii

Biosynthesis

Contact Info

Product

Resources

About

2,2',2″-Tripyrrylmethenes^1,2