Polycyclic compounds beyond the propellanes and fenestranes: [m.n.o.p.q]centropenta- and [m.n.o.p.q.r]centrohexacyclanes

Kuck, Dietmar; Krause, Ralph A.; Gestmann, Detlef; Posteher, Frank; Schuster, Andreas

doi:10.1016/s0040-4020(98)00198-7

Cited by 15 publications

(18 citation statements)

References 35 publications

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“…Thus, centropentaindane 10 was obtained in excellent yield (88% overall yield starting from triindane 6) [47,102]. A similar conversion via tribenzo-[5.5.5.5]fenestrane 259 furnished pentabenzohexaquinane 260, the highest member of the family of partially benzoannelated centrohexaquinanes [42,123]. Centropentaindane 10 is a high-melting compound bearing two residual bridgehead C-H bonds.…”

Section: Centropentaindanementioning

confidence: 99%

“…Tetrabromide 244 served as the base to prepare a number of other bridgehead-heterofunctionalized fenestrindanes, such as the tetraazide 250 [121], from which the tetraamine 251 [98,123] has become accessible. In many cases, the S N 1-type conversions of 244 parallel those of tribromotribenzotriquinacenes such as 142, as do the syntheses of 244 and 142 from the parent centropolyindanes (cf.…”

Section: 243mentioning

confidence: 99%

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The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

Kuck

1998

Topics in Current Chemistry

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Centropolyindanes constitute a complete family of arylaliphatic polycyclic hydrocarbons containing several indane units. Mutual fusion of the five-membered rings leads to three-dimensional, carbon-rich molecular frameworks bearing a central carbon atom, such as benzoannelated [3.3.3]propellanes, triquinacenes, and [5.5.5.6]-and [5.5.5.5]fenestranes. In this review, the structural concept of centropolyindanes is contrasted to other fused indane hydrocarbons. Besides the syntheses of the parent centropolyindanes and recently described related indane hydrocarbons, the preparation of a large variety of bridgehead and arene substituted centropolyindanes is presented including strained, heterocyclic, and centrohexacyclic derivatives. In appropriate cases, the particular reactivity and some structural features of these unusual, sterically rigid polycyclic compounds are pointed out.

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Section: Centropentaindanementioning

confidence: 99%

Section: 243mentioning

confidence: 99%

The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

Kuck

1998

Topics in Current Chemistry

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“…[23] [24] Howtons. This is another indication of the large anisotropic ef-ever, no cyclization products were found in these experifects operating in this highly crowded propellane alcohol.…”

Section: Benzylidenetriptindanesmentioning

confidence: 99%

Phenanthro[1.10]-Annelated [3.3.3]Propellanes by Cyclodehydrogenation Reactions of Mono-, Di-, and Tribenzylidenetriptindanes

Hackfort

Kuck

1999

Eur. J. Org. Chem.

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“…In another mathematical view, centrohexaindane ( 1 ) represents the highest member of two families of centropolycyclanes . One is the centropolyindanes, which bear several indane units fused to one another at the central carbon .…”

Section: Introductionmentioning

confidence: 99%

An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo‐Annelated Centropolyquinanes and Ozonolytic Abbau

et al. 2017

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This study presents a potential experimental approach to the still elusive topologically nonplanar (K5) parent hydrocarbon, centrohexaquinane (1), by a construction‐dismantling (aufbau–abbau) strategy via electron‐rich aromatic centropolyindanes. A series of veratrole‐based centropolyindanes are synthesized and subjected to ozonolytic degradation. These include the 2,2′‐spirobiindanes 30–32, fuso‐diindane 33, triptindanes 34–36, tribenzotriquinacene 37, and tetramethoxycentrohexaindane 9. Spirane 30 and propellane 36 are characterized by X‐ray structure analysis. Ozonolysis of 32 and 33 gives a keto ester (59) and a dimethyl muconate (60), respectively. Dimethoxytriptindane 34 gives a [3.3.3]propellane‐cis,cis‐muconate (61) in good yield, the stereochemistry of which is determined by X‐ray structure analysis. Tetramethoxytriptindane 35 gives the [3.3.3]propellane‐bis‐muconate 62 along with a [3.3.3]propellane‐dialdehyde‐muconate (63). Hexamethoxytriptindane 36 furnishes three products of mainly intra‐dimethoxy cleavage, with the [3.3.3]propellane‐tris‐muconate 64 as the major component. X‐ray structure analysis of 64 reveals molecular C3 symmetry and all‐cis,cis stereochemistry of the three muconate groups. Hexamethoxytribenzotriquinacene 37 gives the triquinacene‐tris‐muconate 68, albeit in very low yield. Ozonolysis of tetramethoxycentrohexaindane 9 affords the bis‐muconate 10 in moderate yield, along with two further centrohexacyclic products of single‐wing degradation.

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Polycyclic compounds beyond the propellanes and fenestranes: [m.n.o.p.q]centropenta- and [m.n.o.p.q.r]centrohexacyclanes

Cited by 15 publications

References 35 publications

The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

The Centropolyindanes and Related Centro-Fused Polycyclic Organic Compounds

Phenanthro[1.10]-Annelated [3.3.3]Propellanes by Cyclodehydrogenation Reactions of Mono-, Di-, and Tribenzylidenetriptindanes

An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo‐Annelated Centropolyquinanes and Ozonolytic Abbau

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