Methano-bridged 10.pi.-electron aromatic annulenes. 4-Methoxy-1,6-methanoisoquinoline

Lipa, William J.; Crawford, H. T.; Radlick, Phillip; Helmkamp, George K.

doi:10.1021/jo00414a004

Cited by 20 publications

(5 citation statements)

References 2 publications

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“…Winstein" several years ago, 60 furnishes a cationic species (presumably via a u-complex) whose 'H-and l3C-NMR spectra show it to have retained the C 2usymmetry of the starting material. The changes in the 'H and l3C chemical shifts associated with the formation of this species are of the same dramatic order of magnitude and in the same direction as those observed in the oxidation of acenes," such as naphthacene (62), to (4n) rr-dications. Hence, it must be concluded that 60 has been oxidized in the super acid solution to the 167Tdication 61, corresponding to 63 in the acene dication series.…”

Section: Hõsupporting

confidence: 54%

“…The changes in the 'H and l3C chemical shifts associated with the formation of this species are of the same dramatic order of magnitude and in the same direction as those observed in the oxidation of acenes," such as naphthacene (62), to (4n) rr-dications. The changes in the 'H and l3C chemical shifts associated with the formation of this species are of the same dramatic order of magnitude and in the same direction as those observed in the oxidation of acenes," such as naphthacene (62), to (4n) rr-dications.…”

supporting

confidence: 54%

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Bridged Annulenes

Vogel

1980

Israel Journal of Chemistry

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The synthesis and aromaticity of 1,6‐methano[10]annulene and its analogues containing a heteroatom bridge suggested the possibility that the homologous series of bridged [4n + 2]annulenes 1, 2, 3, etc., formally derived from the acene series, could be developed. In the pursuit of this concept a set of systematically bent bridged [14]annulenes which permitted a scrutinization of the steric prerequisite of the Hückel rule — the requirement of a planar ring skeleton — were built up. Moreover, a new synthetic strategy based on the synthon cycloheptatriene‐1,6‐dicarboxaldehyde has provided access to the two next higher homologues (syn‐series) of 1,6‐methano[10]annulene, i.e., syn‐1,6:8,13‐bismethano[14]annulene and syn, syn‐1,6:8,17:10,15‐trismethano[18]annulene, respectively.

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Section: Hõsupporting

confidence: 54%

supporting

confidence: 54%

Bridged Annulenes

Vogel

1980

Israel Journal of Chemistry

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“…A trigonal bipyramidal geometry about the sulphur atom was suggested to explain the A related S'" heterocycle is the sulphurane (197). 146 The fused dithiolium salt (198) on (196) (197) (198) reduction formed a very stable and persistent free radical, which showed no tendency to dimerise in The iodine heterocycles (199) and ( 200) have been Finally in this Section, we have this year's Puzzle Corner. Maleic anhydride is refluxed in acetic acid with 2-aminopyridine, followed by hydrolysis (reflux in…”

Section: Four-membered Ringsmentioning

confidence: 97%

Chapter 11. Heterocyclic chemistry

Boulton¹

1978

Annu. Rep. Prog. Chem., Sect. B

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“…The title compounds were prepared by the Beckmann rearrangement of diepoxy[l5]-and triepoxy[l7]-annulenone oximes (2) and (111, respectively; 4: 7,lO : 13-diepoxy-l-aza[l6]annulene (5) exists as two tautomers, the keto form (5a) and the dipolar form (5b), forming a paratropic 16n system; 3 : 6,9 : 12,15 : 18-triepoxy-2-chloro-1-aza-…”

mentioning

confidence: 99%

“…168-170°C (EtOH), violet prisms, mlz 253 (M+)]. Surprisingly, the electronic spectrum of (5) [A, , , , 548 nm (in n-hexane)] and (7)9 1530 nm (in n-hexane)],…”

mentioning

confidence: 99%