Trinacrene – a Product of Structure‐Directed Synthesis

Ashton, Peter R.; Isaacs, Neil S.; Kohnke, Franz H.; D'Alcontres, Guglielmo Stagno; Stoddart, J. Fraser

doi:10.1002/anie.198912611

Cited by 43 publications

(14 citation statements)

References 26 publications

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“…The groups of Stoddart and Vo ¨gtle contributed also with multistep syntheses to this field, unfortunately, overall yields weren't never higher than 2%. 26 A real breakthrough was made by Moore and co-workers, who synthesized macrobicycle 17 (Fig. 3) in a multistep Sonogashira-Hagihara approach in 32% overall yield.…”

Section: Cage Synthesis By Irreversible Bond Formationmentioning

confidence: 99%

Organic cage compounds – from shape-persistency to function

2014

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Defined cavities are found in biological systems, such as in enzymes to accelerate specific reactions with specific molecular targets, or as transport containers for molecular cargoes. Chemists have been inspired by those phenomena found in nature and synthesized defined cage compounds for different purposes, such as for stabilizing reactive intermediates, running reactions within the cavities or studying recognition events. However, most cage compounds are based on the coordination of metal ions, and only a few are charge neutral. Purely organic cages are usually charge neutral and more stable due to existing covalent bonds. Covalent bonds can be made in two ways, applying irreversible reactions or reversible reactions. By introducing dynamic covalent chemistry (DCC), cages have become accessible in good yields from rather simple precursors. Here, we compare both methods and highlight those that give very good yields. Furthermore, the use of organic cage compounds in sorption, recognition, sensing, separation and stabilization of molecules will be discussed.

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Section: Cage Synthesis By Irreversible Bond Formationmentioning

confidence: 99%

Organic cage compounds – from shape-persistency to function

2014

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“…10 As mentioned above we have previously generated and trapped synthetic equivalents of naphthodiynes 5, 6, and 7 to afford the corresponding PAHs 8-10 after deoxygenation ( Figure 1). 4 However, the difficulty of generating tris-arynes is well documented, [11][12][13] and a search of the literature returned no examples in which 1,3,5-benztriyne or a naphthotriyne had been generated from halogenated arenes or synthetic analogues and trapped in a Diels-Alder reaction.…”

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confidence: 98%

Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene

2015

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A new synthesis of dibenzo[a,c]anthracene (4) is described that features the generation, from tetrabromo-bis-triflate 1 and phenyllithium, of a 1,3,6-naphthotriyne (2) synthetic equivalent that is trapped with 3 equiv of furan to form Diels-Alder tris-adduct 3. A subsequent two-step deoxygenation of 3 represents the first synthesis of dibenz[a,c]anthracene (4) that involves a tandem aryne Diels-Alder cycloaddition-deoxygenation strategy.

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“…42 -44 However, in part as a consequence of the nonreversibility of the majority of most classical organic reaction types, such cavity-containing products have tended to be obtained in quite low overall yield. 42 For example, the interesting cage trinacrene 1 (Scheme 2.1), which was proposed as a suitable host for a range of organic, organometallic, and inorganic guests, 45 was prepared in a conventional four-step synthesis starting from furan and hexabromobenzene in an overall yield of less than 0.01%! 42,46 In view of the above propensity for conventional synthetic procedures to result in low overall yields, the use of a template strategy provides a potential means for assisting the formation of a particular cavity-containing product in higher yield.…”

Section: Organic Cage Systemsmentioning

confidence: 99%