Straining strained molecules - I. The synthesis of the first cyclophane within a cyclophane - [2,2]paracyclo ([2,2]metacyclophane)

Mitchell, Reginald H.; Carruthers, Robert J.; Zwinkels, Joanne C.

doi:10.1016/s0040-4039(00)91740-4

Cited by 30 publications

(8 citation statements)

References 15 publications

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“…two-decade period starting in the mid 1970s, feature a pyrene system that is held in a face-to-face orientation with respect to either a second pyrene system or a different aromatic system of similar size. 33,35,[52][53][54][55][56][57] The only notable departure from the standard Type I cyclophane chemistry was with the synthesis of 71 and 72. 57 The pyrenophanes 30, 68 and 70 form an interesting series, in which the two pyrene systems are increasingly bent, albeit not over a particularly large range (θ = 0°, 19.0° and 37.9° for 70, 68 and 30, respectively).…”

Section: Figurementioning

confidence: 99%

“…two-decade period starting in the mid 1970s, feature a pyrene system that is held in a face-to-face orientation with respect to either a second pyrene system or a different aromatic system of similar size. 33,35,[52][53][54][55][56][57] The only notable departure from the standard Type I cyclophane chemistry was with the synthesis of 71 and 72. 57 Here, the key cyclophane-forming reactions took place between naphthalene 1,4,5,8-tetracarboxcylic dianhydride (74) and 2,7bis(o-aminoalkyl)-4,5,9,10-tetrahydropyrenes 73a-b (Scheme 14).…”

Section: Cyclophanes Containing Pahs With Four or More Ringsmentioning

confidence: 99%

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Cyclophanes containing large polycyclic aromatic hydrocarbons

2015

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Cyclophanes have been firmly entrenched as a distinct class of compounds for well over half a century. The two main factors that have kept this field of chemistry going so strongly for such a long time are tremendous structural diversity and the interesting behaviour that is often observed. Although a very large number cyclophanes has been reported, only a very small proportion of them contain polycyclic aromatic systems that can be thought of as "large", i.e. with ≥4 rings. This Review puts the spotlight on such cyclophanes, illuminating both the chemistry that was used to synthesize them and what was learned from studying them. Context for the main body is provided by the careful consideration of the anatomy of a cyclophane and the classification of general synthetic approaches. The subsequent sections cover eleven different PAHs and are organized primarily according to increasing size of the aromatic system, starting with pyrene (C16, the only large polycyclic aromatic system to have been incorporated into numerous cyclophanes) and ending with hexabenzo[bc,ef,hi,kl,no,qr]coronene (C42).

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Section: Figurementioning

confidence: 99%

“…two-decade period starting in the mid 1970s, feature a pyrene system that is held in a face-to-face orientation with respect to either a second pyrene system or a different aromatic system of similar size. 33,35,[52][53][54][55][56][57] The only notable departure from the standard Type I cyclophane chemistry was with the synthesis of 71 and 72. 57 Here, the key cyclophane-forming reactions took place between naphthalene 1,4,5,8-tetracarboxcylic dianhydride (74) and 2,7bis(o-aminoalkyl)-4,5,9,10-tetrahydropyrenes 73a-b (Scheme 14).…”

Section: Cyclophanes Containing Pahs With Four or More Ringsmentioning

confidence: 99%

Cyclophanes containing large polycyclic aromatic hydrocarbons

2015

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“…101,102 The cycloisomerisation of [2,2]metacyclophanes has found its main synthetic applications in the preparation of [2,2]pyrenophanes such as 133 (Scheme 27). [103][104][105] Meanwhile, the valence isomerisation/dehydrogenation of [2,2]metacyclophane-1,9-dienes has proved especially useful for the synthesis of pyrenophanes containing strained pyrene moieties, of general form 134. As shown in Scheme 27 the method allows the framework of the pyrenophane to be constructed via unstrained macrocyclic precursors.…”

Section: Transannular Ring Closure Of [22]metacyclophanesmentioning

confidence: 99%

Synthesis of substituted pyrenes by indirect methods

2014

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The pyrene nucleus is a valuable component for materials, supramolecular and biological chemistry, due to its photophysical/electronic properties and extended rigid structure. However, its exploitation is hindered by the limited range of methods and outcomes for the direct substitution of pyrene itself. In response to this problem, a variety of indirect methods have been developed for preparing pyrenes with less usual substitution patterns. Herein we review these approaches, covering methods which involve reduced pyrenes, transannular ring closures and cyclisations of biphenyl intermediates. We also showcase the diverse range of substituted pyrenes which have been reported in the literature, and can serve as building blocks for new molecular architectures.

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“…[2.2](2,7)Pyrenophane (183) was first prepared by Misumi et al m in 1975, and this report was followed almost simultaneously by accounts of the preparation of the same compound by independent groups in Victoria, Canada 174 and Heidelberg. 175 176 The synthetic routes to the pyrene moieties were invariably based on transannular reactions of metacyclophanes 177 ; for example, [2.2]metacyclophane (180) on reaction with bromine, with a small amount of iron powder, gave the tetrahydropyrene derivative 181.…”

Section: A Pyrenesmentioning

confidence: 99%

Condensed Benzenoid Cyclophanes

Reiss

1983

Organic Chemistry: A Series of Monographs

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Straining strained molecules - I. The synthesis of the first cyclophane within a cyclophane - [2,2]paracyclo ([2,2]metacyclophane)

Cited by 30 publications

References 15 publications

Cyclophanes containing large polycyclic aromatic hydrocarbons

Cyclophanes containing large polycyclic aromatic hydrocarbons

Synthesis of substituted pyrenes by indirect methods

Condensed Benzenoid Cyclophanes

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