A simple methodology for aza-annulene synthesis: preparation and propreties of 2,15-diethoxycarbonyl-4,7:10,13-diepoxy-2-cis,8-cis, 14-cis-aza[15]annulene

Ogawa, Haru; Kumemura, Megumi; Imoto, Taiji; Miyamoto, Izumi; Kato, Hidefumi; Taniguchi, Yōichi

doi:10.1039/c39840000423

Cited by 5 publications

(2 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Such systems are not unknown experimentally though, and a nearly planar [4,9]methano‐bridged aza[11]annulene (a pyrrole or 1H‐azepine homologue) and an aza[15]annulene annelated with furan rings have been reported 17,18. At the time of their characterization, the observed paratropicity of the 12 and 16π electron conjugated molecules was not unexpected 12,13.…”

Section: Introductionmentioning

confidence: 99%

Neutral Möbius Aromatics: Derivatives of the Pyrrole Congener Aza[11]annulene as Promising Synthetic Targets

Mauksch

Tsogoeva

2008

Eur J Org Chem

View full text Add to dashboard Cite

Amino‐ and methyl‐disubstituted derivatives of an aromatic 12π electron pyrrole homologue Möbius 1H‐aza[11]annulene are predicted computationally at the B3LYP/6‐31G* level of theory to be distinctly aromatic and a neutral ground state on its potential surface. The parent annulene has a nonaromatic conformation, which is 6.0 kcal mol–1 lower in energy at the CCSD(T)/D95*//B3LYP/6‐31G* level of theory than a structurally very similar Möbius conformation. After derivatization, however, geometry optimizations of the two lowest‐energy – Möbius and non‐Möbius – heteroannulene conformations both converged two a single Möbius minimum, whereas two (Möbius and non‐Möbius) distinct difluoro‐ substituted species could be located 1.8 kcal mol–1 apart in energy at the B3LYP level. The Möbius minimum is 7.5 kcal mol–1 lower in energy at the coupled cluster level than a “Hückel topology” form derived from a known bridged 1H‐[4,9]methano[11]annulene. Several possible reactive modes are investigated in order to assess the relative stability of the Möbius parent annulene. In addition, we report formal novel examples for charged and neutral Möbius triplet aromatic annulenic and heteroannulenic systems, some of which also exhibit distinct aromatic properties. Further fundamental insights into the phenomenon of “Möbius aromaticity” are suggested. The aromaticity of Möbius annulenes is for the first time linked to wavefunction boundary conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

show abstract

Section: Introductionmentioning

confidence: 99%

Neutral Möbius Aromatics: Derivatives of the Pyrrole Congener Aza[11]annulene as Promising Synthetic Targets

Mauksch

Tsogoeva

2008

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…These were separated by column chromatography (SO2, CH2C12-EtOH) and characterized (in the sequence of the elution); oxime (2) [m.p. 180 "C (n-hexane-benzene), orange prisms, m/z 253 ( M + ) , 8.5%], an isoxazoline derivative (3) [m.p. 145-146°C (n-hexane), yellow prisms, m/z 253 (M+), 18%], and a hydroxylamine adduct (4) [m.p.…”

mentioning

confidence: 99%

4:7,10:13-Diepoxy-1-aza[16]annulene and 3:6,9:12,15:18-triepoxy-2-chloro-1-aza-[18]annulene as the first examples of oxygen-bridged aza-[4n]- and -[4n+ 2]annulenes

Ogawa¹,

Kumemura²,

Imoto³

et al. 1987

J. Chem. Soc., Chem. Commun.

Self Cite

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: A SIMPLE METHODOLOGY FOR AZAANNULENE SYNTHESIS: PREPARATION AND PROPERTIES OF 2,15‐DIETHOXYCARBONYL‐4,7:10,13‐DIEPOXY‐2‐CIS,8‐CIS,14‐CIS‐AZA(15)ANNULENE

Ogawa¹,

Kumemura²,

Imoto³

et al. 1984

Chemischer Informationsdienst

View full text Add to dashboard Cite

show abstract

A simple methodology for aza-annulene synthesis: preparation and propreties of 2,15-diethoxycarbonyl-4,7:10,13-diepoxy-2-cis,8-cis, 14-cis-aza[15]annulene

Abstract: The synthesis and properties of the titled compound (9) are described; (9) was prepared by the thermolysis of the vinyl azide (5) in 70% yield, and no furopyrrole derivatives were formed.

Cited by 5 publications

References 3 publications

Neutral Möbius Aromatics: Derivatives of the Pyrrole Congener Aza[11]annulene as Promising Synthetic Targets

Neutral Möbius Aromatics: Derivatives of the Pyrrole Congener Aza[11]annulene as Promising Synthetic Targets

4:7,10:13-Diepoxy-1-aza[16]annulene and 3:6,9:12,15:18-triepoxy-2-chloro-1-aza-[18]annulene as the first examples of oxygen-bridged aza-[4n]- and -[4n+ 2]annulenes

ChemInform Abstract: A SIMPLE METHODOLOGY FOR AZAANNULENE SYNTHESIS: PREPARATION AND PROPERTIES OF 2,15‐DIETHOXYCARBONYL‐4,7:10,13‐DIEPOXY‐2‐CIS,8‐CIS,14‐CIS‐AZA(15)ANNULENE

Contact Info

Product

Resources

About