Efficient Synthesis of Heteroradialenes by SN′ Reaction

Gleiter, Rolf; Röckel, Harald; Irngartinger, Hermann; Oeser, Thomas

doi:10.1002/anie.199412701

Cited by 14 publications

(11 citation statements)

References 17 publications

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“…19,191 Whereas the reaction of 255 with Na 2 S gave an isolable amount of the trimeric 251, the selenium analogue was not observed during the reaction with Na 2 Se.…”

Section: Expanded Radialenes With Heteroatom Spacersmentioning

confidence: 74%

Oligomeric and Polymeric Systems with a Cross-conjugated π-Framework

2006

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“…19,191 Whereas the reaction of 255 with Na 2 S gave an isolable amount of the trimeric 251, the selenium analogue was not observed during the reaction with Na 2 Se.…”

Section: Expanded Radialenes With Heteroatom Spacersmentioning

confidence: 74%

Oligomeric and Polymeric Systems with a Cross-conjugated π-Framework

2006

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“…The extent of cross-conjugation in [n]radialenes has attracted substantial theoretical and experimental study [92,93] and their versatile molecular scaffolds are finding application in the construction of advanced functional materials. [94,95] Upon insertion of ethane-1,2-diyl (ÀCCÀ) or buta-1,3-diyne-1,4-diyl (ÀCCÀCCÀ), fragments between each pair of vicinal exo-methylene units in the framework of [n]radialenes, a new class of cross-conjugated macrocycles with extended all-carbon cores, the expanded radialenes, is obtained, of which the first representatives, the perethynylated derivatives 14-16 ( Fig. 3) were reported in 1994.…”

Section: Expanded Radialenes and Radiaannulenesmentioning

confidence: 99%

All‐Carbon Scaffolds by Rational Design

2010

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The search for new molecular and regular polymeric allotropes of carbon has greatly stimulated the preparation and investigation of pi-conjugated acetylenic macrocycles, which often represent substructures of proposed 2D carbon networks. Perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes with large, multi-nanometer-sized all-carbon cores are potent electron acceptors, and their optoelectronic as well as stability and solubility properties are greatly enhanced by peripheral donor substitution. Acetylenic scaffolding into three dimensions has generated an expanded cubane with a C(56) core, the first representative of a new class of "platonic" objects. Exceptional chiroptical properties displayed by enantiomerically pure alleno-acetylenic, shape-persistent macrocycles promise fascinating perspectives for the development of molecular and supramolecular chiroptical materials.

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“…These compounds were prepared under high-dilution conditions.S pecifically,s low addition of DEBD precursor 22 to the reagent mixture gave cyclotrimer 25 (an expanded [6]radialene) as the major product, with even slower addition giving rise to mixtures richer in the cyclodimer 24 (an Figure 3. The known iso-polydiacetylenes (iso-PDAs) and iso-polytriacetylenes (iso-PTAs) "expand" ad endralene by separating individual C=C units.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of 2,3‐Diethynyl‐1,3‐Butadienes

2020

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The first general preparative access to compounds of the 2,3‐diethynyl‐1,3‐butadiene (DEBD) class is reported. The synthesis involves a one‐pot, twofold Sonogashira‐type, Pd0‐catalyzed coupling of two terminal alkynes and a carbonate derivative of a 2‐butyne‐1,4‐diol. The synthesis is broad in scope and members of this structural family are kinetically stable enough to be handled using standard laboratory techniques at ambient temperature. They decompose primarily through heat‐promoted cyclodimerizations, which are impeded by alkyl substitution and accelerated by aryl or alkenyl substitution. An iterative sequence of these unprecedented Sonogashira‐type couplings generates a new type of expanded dendralene. A suitably substituted DEBD carrying two terminal alkyne groups undergoes Glaser–Eglinton cyclo‐oligomerization to produce a new class of expanded radialenes, which are chiral due to restricted rotation about their 1,3‐butadiene units. The structural features giving rise to atropisomerism in these compounds are distinct from those reported previously.

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Efficient Synthesis of Heteroradialenes by SN′ Reaction

Abstract: COMMUNICATIONS calculated positions bith l',,,, = 1.3 L',,, for parent atoms. Final R = 0.095.

Cited by 14 publications

References 17 publications

Oligomeric and Polymeric Systems with a Cross-conjugated π-Framework

Oligomeric and Polymeric Systems with a Cross-conjugated π-Framework

All‐Carbon Scaffolds by Rational Design

Synthesis and Properties of 2,3‐Diethynyl‐1,3‐Butadienes

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