Functionalized Enantiomerically Pure [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes

Müller-Bötticher, Hermann; Fessner, Wolf‐Dieter; Melder, Johann‐Peter; Prinzbach, Horst; Gries, Stefan Τh.; Irngartinger, Hermann

doi:10.1002/cber.19931261018

Cited by 10 publications

(2 citation statements)

References 109 publications

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“…[46] However, the seemingly trivial transformation 39 Ǟ 41 proved tricky. Ultimately, the Fetizon procedure [47] was once more [48] found to be of practical use, superior to various procedures that had been severely hampered by side reactions (primarily bridging in the eight-membered ring [49] ).…”

Section: Introductionmentioning

confidence: 99%

Proximate, “Parallel‐In‐Plane” Preoriented Bis(diazenes) − In‐Plane Delocalized Bis(homoconjugated) 4N/5(6)e Anions

et al. 2003

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Synthetic details are presented for a series of more or less rigid, “parallel‐in‐plane” preoriented bis(diazenes), with N=N/N=N distances (d) of 3.3−2.9 Å and interorbital angles (ψ) of 142−164° (X‐ray crystal structures). DFT calculations (B3LYP/6−31G*) and one‐/two‐electron reduction experiments with the two least preoriented, most “distant” bis(diazenes) (dN=N/N=N ca. 3.3 Å; ψ 142−146°) provide more insight into the structural prerequisites for bis(homoconjugative) in‐plane electron delocalization in 4N/5e radical anions and 4N/6e dianions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Introductionmentioning

confidence: 99%

Proximate, “Parallel‐In‐Plane” Preoriented Bis(diazenes) − In‐Plane Delocalized Bis(homoconjugated) 4N/5(6)e Anions

et al. 2003

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“…Examples of the successful Perkow reaction also include chlorofluoro ketones, e.g. 1,3-dichloro-1,1,3,3-tetrafluoroacetone,[ 7 ] α-halonitroalkanes, and in rare cases also polycyclic compounds[ 8 ] such as 3,3-dichloro-1-methylquinoline-2,4(1 H ,3 H )-dione. [ 9 ] In the Perkow reaction of halocompounds, the observed leaving groups were the halogen anions.…”

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confidence: 99%

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds

Paleta¹,

Pomeisl²,

Kafka³

et al. 2005

Beilstein J. Org. Chem.

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Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the first observed leaving group. This observation restricts the application of the intramolecular Horner-Wadsworth-Emmons synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of fluorinated but-2-enolide rings.

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Electronic Interactions in Saturated and Unsaturated [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes — PE‐Spectroscopic Investigations

et al. 1993

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The He(1)-PE spectra of the parent [1.1.1]-, [2.1.1]-, [2.2.1]-, and [2.2.2]triblattanes 1-4, of their unsaturated or ketonic congeners 5-13 and benzo derivatives 14-20 have been recorded. For 1-4, the energy difference between the highest occupied orbitals (e" and a' mainly localized at the central bicyclo-12.2.2loctane unit) and the subsequent MOs increases with increasing number of ethano bridges. This observation is rationalized by using a first-order perturbation-theoretical approach.Orbitals of nonconjugated x-systems can interact with each other by a "through-space'' (OITS) and/or "through-bond'' mode (OITB)"]. The OITS mode is sometimes subdivided into the terms "homoconjugation"L21 and "spiroc~njugation"[~~. A prerequisite common to all of these OITS types is the spatially confined proximity and orientation of the nonconjugated x-fragment~[~I which can be achieved by their imbedding into a suitable o-system. In fact, record OITS values (2.2 eV) approaching that of classical R,T[ conjugation have been recorded for D2,,-bissecododecahedradiene~'~], in which the specific carbon skeleton enforces unu- 63

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Functionalized Enantiomerically Pure [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes

Cited by 10 publications

References 109 publications

Proximate, “Parallel‐In‐Plane” Preoriented Bis(diazenes) − In‐Plane Delocalized Bis(homoconjugated) 4N/5(6)e Anions

Proximate, “Parallel‐In‐Plane” Preoriented Bis(diazenes) − In‐Plane Delocalized Bis(homoconjugated) 4N/5(6)e Anions

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds

Electronic Interactions in Saturated and Unsaturated [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes — PE‐Spectroscopic Investigations

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