Novel adamantane-bearing anilines and properties of their supramolecular complexes with β-cyclodextrin

Vícha, Robert; Rouchal, Michal; Kozubková, Zuzana; Kuřitka, Ivo; Marek, Radek; Branná, Petra; Čmelík, Richard

doi:10.1080/10610278.2011.593628

Cited by 18 publications

(20 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the solid state, X-ray crystallography reveals that 1-adamantanol forms both type I and type II complexes with a methylated βCD. 13 In contrast, most of the abovementioned studies of complexes in solution report the formation of a single type of complexes, most of them type I and only a few type II complexes 16,17,23 . It is possible, however, that many of the investigated complexes in solution form both type I and type II complexes.…”

Section: Introductionmentioning

confidence: 93%

Charge Determines Guest Orientation: A Combined NMR and Molecular Dynamics Study of β-Cyclodextrins and Adamantane Derivatives

Schönbeck

2018

J. Phys. Chem. B

View full text Add to dashboard Cite

The strong binding of the adamantyl moiety to the cavity of β-cyclodextrin makes it a common binding motif in supramolecular chemistry and a common model system. Despite the attention, there are still unresolved questions regarding the orientation of the adamantane derivatives in the inclusion complexes-do they protrude from the wide or narrow opening of the cyclodextrin hosts? A combined analysis of ROESY NMR and molecular dynamics simulations allows the conclusion that positively charged adamantane derivatives are oriented with the hydrophilic group protruding from the wider opening of the cyclodextrin, while negatively charged adamantane derivatives form two coexisting types of complexes where the hydrophilic group respectively protrudes from the wide and narrow opening. Interestingly, structural modifications of the cyclodextrin host only have a slight impact on the guest orientation.

show abstract

Section: Introductionmentioning

confidence: 93%

Charge Determines Guest Orientation: A Combined NMR and Molecular Dynamics Study of β-Cyclodextrins and Adamantane Derivatives

Schönbeck

2018

J. Phys. Chem. B

View full text Add to dashboard Cite

show abstract

“…Preparation of 1,3-dithiolanes 13a , b : Both compounds were prepared from commercial methyl (trimethylsilyl) ketone or phenyl (trimethylsilyl) ketone [35], respectively, by treatment with 1,2-ethanedithiol in the presence of BF 3 ·Et 2 O following a literature protocol [36]. …”

Section: Methodsmentioning

confidence: 99%

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

Mlostoń

Pipiak

Hamera-Fałdyga

et al. 2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl-4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at −75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2 at −60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. −45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3-dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

show abstract

“…For the preparation of the title compound, see Vícha et al (2011). For crystallographic data for similar aryl-substituted 1,3-dithianes, see: Fun et al (2009a,b); Samas et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

2-Methyl-2-(3-nitrophenyl)-1,3-dithiane

2012

Self Cite

View full text Add to dashboard Cite

The title compound, C11H13NO2S2, contains a 1,3-dithiane ring in an almost ideal chair conformation with the following puckering parameters: Q = 0.7252 (15) Å, θ = 6.71 (13) and ϕ = 50.4 (11)°. The benzene ring occupies an axial position at the dithiane ring. The nitro group is almost coplanar with the benzene ring [O—N—C—C = −3.2 (2)°]. The molecule has an L-shape with a C—C—C—C torsion angle of −74.15 (17)° for the atoms of the methyl group and the dithiane–benzene linkage. The crystal packing is stabilized only via weak non-specific van der Waals interactions.

show abstract

Novel adamantane-bearing anilines and properties of their supramolecular complexes with β-cyclodextrin

Cited by 18 publications

References 28 publications

Charge Determines Guest Orientation: A Combined NMR and Molecular Dynamics Study of β-Cyclodextrins and Adamantane Derivatives

Charge Determines Guest Orientation: A Combined NMR and Molecular Dynamics Study of β-Cyclodextrins and Adamantane Derivatives

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

2-Methyl-2-(3-nitrophenyl)-1,3-dithiane

Contact Info

Product

Resources

About