The first dimers derived from mesoionic 1,3-dithiolones

Die Synthese und spektroskopischen Eigenschaften der neuen Titelverbindungcn vom Typ 6 und 17, die m e i identische mesoionische Systeme iiber die 5-Stellungen gebunden enthalten, sowie die Polymerisation zu 18 und die Dimerisierung von 6c-e zu 2Oa -c werden beschrieben.In einer vorangegangenen Mitteilung') berichteten wir erstmals uber die Darstellung und physikalischen Eigenschaften von 2,2'-verbruckten Bis(l,3-dithiolylium-4-olaten), die fur die Synthese neuartiger Makroheterocyclen interessant sind. Mit der gleichen Zielsetzung synthetisierten wir im weiteren Verlauf dieser Untersuchungen auch neue zweikernige mesoionische 1,3-Dithiol-Cone, die iiber die 5-Stellungen miteinander verbriickt sind.Nachstehend beschreiben wir die Synthese und spektroskopischen Eigenschaften dieser neuen Titelverbindungen vom Typ 6 und 17 sowie das interessante Polymerisationsund Dimerisationsverhalten einiger Vertreter 6.

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“…462 (16,Mi).3I3(8,M+ -C O -C6HJS),221(2,313 -C O -2 S), 164 (2, M' -2 CO -2 C~HSCS), 121 (100. C~H J C S~) , 77…”

Section: Synthese Der Vorstufenmentioning

confidence: 99%

Synthese und physikalische Eigenschaften erster 5, 5′‐verbrückter Bis(1,3‐dithiolylium‐4‐olate

Gotthardt

Pflaumbaum

1987

Chem. Ber.

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The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Rickborn

1998

Organic Reactions

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This review (Part II) is topically organized around the dienophile that is generated in a retro [4 + 2] reaction, and to the extent possible follows the principles adopted for Part I, which covers reactions in which both dienophile bonding centers are carbon atoms. The present chapter encompasses retro–Diels–Alder (rDA) reactions in which one or both of the dienophile reaction centers are heteroatoms. Any of the other atoms in the starting material (cycloadduct) may be carbon or heteroatom. Substituents on all positions are encompassed, and any bond order available to any oxidation state of an element is included, as is bonding to non‐nearest neighbor atoms (e.g., bicyclics). The reader is directed to Part I (Vol. 52) for general discussion of the rDA reaction, the features that affect rates and outcome, and the use of acids, bases, other catalysts, and scavengers. Certain subclassifications (e.g., processes proposed under MS conditions, polymer applications) of rDA reactions have been omitted from both sections; these topics are listed in the Introduction to Part I. Citations to over 100 reviews on various aspects of the rDA reaction are collected at the beginning of the References to Part I. Those that are especially pertinent to Part II will be repeated here, in the context of the particular dienophile under discussion. The decision to split the review of the rDA reaction into two parts was based on the volume of literature encountered, as outlined in the Introduction to Part I. Active literature searching was concluded for both Parts in April 1995, although occasional more recent references have been included.

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Preparation of Thiophenes by Ring‐Closure Reactions and from other Ring Systems

Gronowitz¹

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The first dimers derived from mesoionic 1,3-dithiolones

Cited by 16 publications

References 8 publications

Synthese und physikalische Eigenschaften erster 5, 5′‐verbrückter Bis(1,3‐dithiolylium‐4‐olate

Synthese und physikalische Eigenschaften erster 5, 5′‐verbrückter Bis(1,3‐dithiolylium‐4‐olate

The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Preparation of Thiophenes by Ring‐Closure Reactions and from other Ring Systems

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