Structural Identification of Products from the Chloromethylation of Salicylaldehyde

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 44-48 ◽  
Author(s):  
Muhammad Bala ◽  
Ebrahim Kadwa ◽  
Holger Friedrich
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution Mass Spectrometry ◽  
Structural Identification ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
X Ray ◽  
Multinuclear Nmr Spectroscopy ◽  
Ir Spectroscopic ◽  
Resolution Mass

In the functionalization of salicylaldehyde to give 5-(chloromethyl)salicylaldehyde, two byproducts [5-(hydroxymethyl)salicylaldehyde and 5,5′-methylenebis(salicylaldehyde)] were also isolated. ­Detailed characterizations and structural analyses of all three products by single-crystal X-ray diffraction, multinuclear NMR spectroscopy, high-resolution mass spectrometry, and IR spectroscopic techniques are presented and discussed. A strategy is presented for the preferential isolation of the two byproducts through column chromatography.

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2009-2018
Author(s):  
Jan-Hendrik Lamm ◽  
Philipp Niermeier ◽  
Leif Körte ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Building Block ◽  
High Resolution Mass Spectrometry ◽  
Cross Coupling ◽  
Easy Access ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

Two Propanediurea-based Cucurbituril Analogues: Bis-ns-TD[8] and NH-ns-TD[4]

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2381-2384
Author(s):  
Qiaochun Wang ◽  
Chunhua Dai ◽  
Yenan Shen
Keyword(s):  
Mass Spectrometry ◽  
1H Nmr Spectroscopy ◽  
High Resolution Mass Spectrometry ◽  
The Other ◽  
Amine Group ◽  
X Ray Diffraction ◽  
Excellent Thermal Stability ◽  
X Ray ◽  
Secondary Amine Group ◽  
Resolution Mass

Two new cucurbituril members, one containing two equivalent cavities and the other having an active secondary amine group, were synthesized by condensation of propanediurea (2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione) with formaldehyde. These two macrocycles exhibit excellent thermal stability, and their structures were confirmed by single-crystal X-ray diffraction, 1H NMR spectroscopy, and high-resolution mass spectrometry.

scholarly journals Synthesis and Molecular Structure of tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate

2014 ◽  
Vol 2014 ◽  
pp. 1-6 ◽  
Author(s):  
Tetsuji Moriguchi ◽  
Suvratha Krishnamurthy ◽  
Toru Arai ◽  
Taisuke Matsumoto ◽  
Koji Araki ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
Amino Acid Ester ◽  
Piperidine Ring ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Resolution Mass

The compound tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a cyclic amino acid ester from the corresponding ethyl 2-amino-4-(2-oxiranyl)butanoate HCl salt via an intramolecular lactonization reaction and was characterized by using 1H NMR spectroscopy and high-resolution mass spectrometry. The product was then recrystallized from dichloromethane/diethyl ether and its structure was determined via single crystal X-ray diffraction analysis. The crystal was found to be of the monoclinic space group P21/c (no. 14) with a = 10.217(2) Å, b = 11.676(3) Å, c = 10.273(3) Å, β = 114.186(13)°, and Dcalc = 1.350 g/cm3 at 123 K. The compound has bicyclo[2.2.2]octane structure including a lactone moiety and a piperidine ring, and the two diastereomers of the molecules are present in a 1 : 1 ratio in the crystal.

Unusual Rearrangement of Naphthalene in the Synthesis of a Novel B8-B8-Bridged Derivative in the [(1,2-C2B9H11)2-3-Co]- Series. X-Ray Structure and 11B NMR Spectra of [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- (CH3)4N+

1997 ◽  
Vol 62 (5) ◽  
pp. 746-751 ◽  
Author(s):  
Andreas Franken ◽  
Jaromír Plešek ◽  
Christiane Nachtigal
Keyword(s):  
Nmr Spectroscopy ◽  
Single Crystal ◽  
Nucleophilic Substitution ◽  
Nmr Spectra ◽  
X Ray Diffraction ◽  
X Ray ◽  
Unusual Rearrangement ◽  
Multinuclear Nmr Spectroscopy ◽  
11B Nmr ◽  
Isolated Compound

On treatment of the [(1,2-C2B9H11)2Co]- ion with naphthalene in presence of AlCl3 a remarkably bridged [8,8'-μ-(CH2-C9H6)-(1,2-C2B9H10)2-3-Co]- ion is obtained as a single isolated compound. The triatomic -CH2-C9H6- bridge is derived from the rearranged naphthalene nucleus. The mechanism of this reaction is obscure but it does resemble the "Electrophile-Induced Nucleophilic Substitution" reported earlier. The structure of the compound was established by multinuclear NMR spectroscopy and by single crystal X-ray diffraction.

scholarly journals Exploring the Structural Chemistry of Pyrophosphoramides: N,N′,N″,N‴-Tetraisopropylpyrophosphoramide

Chemistry ◽  
2021 ◽  
Vol 3 (1) ◽  
pp. 149-163
Author(s):  
Duncan Micallef ◽  
Liana Vella-Zarb ◽  
Ulrich Baisch
Keyword(s):  
Crystal Structure ◽  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
Room Temperature ◽  
Intermolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
X Ray

N,N′,N″,N‴-Tetraisopropylpyrophosphoramide 1 is a pyrophosphoramide with documented butyrylcholinesterase inhibition, a property shared with the more widely studied octamethylphosphoramide (Schradan). Unlike Schradan, 1 is a solid at room temperature making it one of a few known pyrophosphoramide solids. The crystal structure of 1 was determined by single-crystal X-ray diffraction and compared with that of other previously described solid pyrophosphoramides. The pyrophosphoramide discussed in this study was synthesised by reacting iso-propyl amine with pyrophosphoryl tetrachloride under anhydrous conditions. A unique supramolecular motif was observed when compared with previously published pyrophosphoramide structures having two different intermolecular hydrogen bonding synthons. Furthermore, the potential of a wider variety of supramolecular structures in which similar pyrophosphoramides can crystallise was recognised. Proton (1H) and Phosphorus 31 (31P) Nuclear Magnetic Resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS) were carried out to complete the analysis of the compound.

Synthesis, characterization, and structures of zircona- and boracyclosiloxanes with ferrocenyl substituents

2002 ◽  
Vol 80 (11) ◽  
pp. 1469-1480 ◽  
Author(s):  
Karena Thieme ◽  
Sara C Bourke ◽  
Juan Zheng ◽  
Mark J MacLachlan ◽  
Fojan Zamanian ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Differential Scanning Calorimetry ◽  
Thermogravimetric Analysis ◽  
Ring Opening ◽  
Ring Opening Polymerization ◽  
The Novel ◽  
X Ray Diffraction ◽  
Scanning Calorimetry ◽  
X Ray ◽  
Multinuclear Nmr Spectroscopy

The novel zirconatetraferrocenylcyclotrisiloxane Cp2Zr(OSiFc2)2O (6), dizirconatetraferrocenylcyclotetrasiloxane [Cp2Zr(OSiFc2)O]2 (7), boratetraferrocenylcyclotrisiloxane (C6H5)B(OSiFc2)2O (8), and diboratetraferrocenylcyclotetrasiloxane [(C6H5)B(OSiFc2)O]2 (9) with ferrocenyl (Fc = Fe(η-C5H4)(η-C5H5)) substituents at silicon have been prepared from the reactions of Cp2Zr(NMe2)2 and PhBCl2 with diferrocenylsilanediol Fc2Si(OH)2 (3) and tetraferrocenyldisiloxanediol [Fc2SiOH]2O (5). The compounds were characterized by mass spectrometry, elemental analysis, UV–vis, IR, Raman, and multinuclear NMR spectroscopy, as well as single crystal X-ray diffraction. Thermogravimetric analysis and differential scanning calorimetry investigation of 6–9 showed that the cycles decompose before they can undergo any thermal ring-opening polymerization. In addition, no polymerization was detected in the presence of either KOSiMe3 or HOTf. The bulky ferrocenyl substituents on the Si atoms are likely to be at least partially responsible for the inability of these heterocycles to undergo ring-opening polymerization. Key words: heterocyclosiloxanes, ferrocenyl.

scholarly journals Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Mousa AlTarabeen ◽  
Georgios Daletos ◽  
Weaam Ebrahim ◽  
Werner E. G. Müller ◽  
Rudolf Hartmann ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
Cell Line ◽  
Marine Sponge ◽  
High Resolution Mass Spectrometry ◽  
Two Dimensional ◽  
Meoh Extract ◽  
L5178y Cell ◽  
Resolution Mass

Chemical investigation of the MeOH extract of the sponge Acanthostrongylophora ingens afforded the new manzamine derivative ircinal E (1), in addition to six known metabolites (2–7). The structure of the new compound was unequivocally elucidated using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. Compounds 1–6 exhibited strong to moderate cytotoxicity against the murine lymphoma L5178Y cell line with IC50 values ranging from 2.8 to 21.7 μM.

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