Distorted Saturated Hydrocarbons

Mlinarić‐Majerski, Kata; Dodziuk, Helena; Gribanova, T. N.; Minyaev, R. M.; Suzuki, Takanori; Takeda, Takashi; Kawai, Hidetoshi; Fujiwara, Kenshu; Lee, Vladimir Y.; Sekiguchi, Akira

doi:10.1002/9783527627134.ch2

Cited by 8 publications

(14 citation statements)

References 380 publications

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“…When the employed ratio of LiTMP: MgBr 2 was 1.5:1, the product ratio raised to 9:1 in favor of 90. This led to the discovery that β-magnesiation was possible with TMPMgBr and/or by (TMP) 2 Mg, referred to as the Hauser base. 82,83 This idea was further extrapolated upon by the Eaton group and these amide bases have demonstrated their utility in organic synthesis.…”

Section: Transmetalationmentioning

confidence: 98%

Cubane: 50 Years Later

et al. 2015

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Section: Transmetalationmentioning

confidence: 98%

Cubane: 50 Years Later

et al. 2015

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“…Scheschkewitz synthesized five-vertex cluster with one naked silicon atom 5 (a silicon analog of tricyclo[2.1.0.0 1,3 ]-pentane) 19 as red crystals in moderate yields by the reaction of triaryldisilenide 6 with 0.25 equiv of SiCl 4 (eq 3). 20 The 29 Si resonance due to the central silicon without substituents appeared at ¹124.8 ppm.…”

Section: Si 5 R 6 Derivativesmentioning

confidence: 99%

“…Molecules with nonclassical or unusual structures, bondings, or electronic properties 1 have attracted many experimental and theoretical chemists because exploration of such molecules is expected not only to lead to discovery of unprecedented reactivity and useful functions but also to have a possibility to evolve the concept of structures and bondings. One of the most fascinating organic molecules bearing nonclassical structure is [1.1.1]propellane A ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…One of the most fascinating organic molecules bearing nonclassical structure is [1.1.1]propellane A ( Figure 1). 2 This molecule has bridgehead carbon atoms with an umbrella-type geometry B 1,3 (shown in boldface) where all bonds point to a hemisphere, which has been often expressed as an inverted (tetrahedral) geometry. The bridgehead CC bond (inverted σ bond) in [1.1.1]propellanes shows considerably high reactivity with biradical (A¤) or ionic (A¤¤) characters compared with normal CC σ bond in normal tetrahedral geometry C because of the poor overlap between orbitals of the bridgehead carbon atoms in the inverted geometry.…”

Section: Introductionmentioning

confidence: 99%

“…One of the interesting features is the existence of the bond-stretch isomers, a short bond (SB) isomer and a long bond (LB) isomer, which differ primarily in the distance between the bridgehead atoms. 1,3 Theoretically, the bridge bond in SB isomer is predicted to be a normal bent σ bond with large RSiSi angle ª and small interflap angle º (Figure 2), while the bond in LB is an inverted σ bond bearing significant singlet biradical character with small ª and large º.…”

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confidence: 99%

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Silicon Compounds with Inverted Geometry around Silicon Atoms

Iwamoto

Ishida

2014

Chemistry Letters

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In the last decade, several stable silicon compounds with nonclassical inverted geometry around silicon atoms have been synthesized. Their unusual structures, bonding, and reactivity have been investigated extensively by X-ray analysis, spectroscopy, and theoretical calculations. In this highlight review, recent progress on chemistry of silicon compounds with inverted geometry around silicon atoms is summarized.

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Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene

Rezvanian

Salimi

Zadsirjan

et al. 2020

Journal of Heterocyclic Chem

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A highly convergent, eco-friendly and straightforward synthesis of new O-fused heterocycles, functionalized indeno[1,2-b]furan derivatives was successfully accomplished through a one-pot four-component cascade reaction involving, ninhydrin, malononitrile, diketene and various primary amines in the presence of a catalytic quantity of triethylamine in ethanol at ambient temperature, in one pot fashion. This new efficient cascade reaction generates two rings by the simultaneous construction of C-N (one), CO (two) and CC (two) multiple bonds, presumably through a sequence of Knoevenagel reaction/ Michael addition/intramolecular O-cyclization and imine-enamine/keto-enol tautomerization. The merits of this protocol are highlighted as utilization of inexpensive commercially accessible starting materials, operational simplicity, atom economy, clean reaction profile, simple work-up procedure being conducted at ambient temperature in relatively short reaction times, preventing chromatographic purification, giving excellent yields, and tolerance to a wide variety of functional groups.

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Distorted Saturated Hydrocarbons

Cited by 8 publications

References 380 publications

Cubane: 50 Years Later

Cubane: 50 Years Later

Silicon Compounds with Inverted Geometry around Silicon Atoms

Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene

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