Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• bromopropargylic alcohols and Cs2CO3. Keywords: acetylenic alcohol; bromoacetylene; 1,3-dioxolan-2-one; phenols; phenoxyketone; Introduction Due to the relative stability, ease of handling and the presence of reactive sites, bromoacetylenes are widely applied in synthetic organic chemistry. They are known to be

• highly selective hydration/acylation of tertiary bromopropargylic alcohols with carboxylic acids promoted by alkali metal carbonates [24]. The reaction proceeds via the ring-opening of 1,3-dioxolan-2-one intermediates formed with hydroxy and alkynyl groups of bromopropargylic alcohol and alkali metal

• , the reaction slowed down and became more selective (Table 1, entries 4 and 5). With Cs2CO3 (1 equiv) at 50–55 °C, the reaction proceeded for 3 h, the yield of the phenoxyhydroxyketone 4a increased up to 55% and 5-phenoxymethylene-1,3-dioxolan-2-one 7, one of the probable intermediates, was isolated in

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• toloxatone derivatives, have been reported to exhibit good affinity for human MAO-A [14]. Five-membered cyclic carbonate (1,3-dioxolan-2-one) (2) and its derivatives are valuable synthetic targets on account of several applications and pertinent properties. They are found in various natural and potential

• in ratios close to 1:1 as shown in Table 2. trans-Stilbene (7d) and cis-stilbene epoxids (7e) in the presence of CSI gave trans-4,5-diphenyl-1,3-dioxolan-2-one (8d), trans-4,5-diphenyloxazolidin-2-one (9d) and cis-4,5-diphenyl-1,3-dioxolan-2-one (8e), cis-4,5-diphenyloxazolidin-2-one (9e

• ), respectively (Table 2). These results show that the relative configuration is preserved. 4-Phenyl-1,3-dioxolan-2-one (8f) and 4-phenyloxazolidin-2-one (9f) were obtained from the reaction of CSI with styrene oxide (7f) showing the regioselective nature of the reaction. In addition, we report the synthesis of

Amino-functionalized (meth)acryl polymers by use of a solvent-polarity sensitive protecting group (Br-t-BOC)

• Helmut Ritter,
• Monir Tabatabai and
• Markus Herrmann

Beilstein J. Org. Chem. 2016, 12, 245–252, doi:10.3762/bjoc.12.26

• chromatography and the 1H NMR spectra of 3a and 3b are shown in Figure 2 and Figure 3. After dissolving monomers 3a and 3b in a polar solvent, they show the above mentioned self-cleaving process yielding the corresponding amine hydrobromide (4a,b) and the cyclic carbonate 4,4-dimethyl-1,3-dioxolan-2-one (5). As

Surprisingly facile CO₂ insertion into cobalt alkoxide bonds: A theoretical investigation

• Willem K. Offermans,
• Claudia Bizzarri,
• Walter Leitner and
• Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 1340–1351, doi:10.3762/bjoc.11.144

• -membered ring intermediate to a six-membered ring. Moreover, Wu et al. studied a) the cycloaddition of ethylene oxide and CO2, catalysed by Ni(PPh3)2 [39], b) the cycloaddition of chloromethyloxirane and CO2, catalysed by Re(CO)5Br [40] and c) the cycloaddition of 4-(phenoxymethyl)-1,3-dioxolan-2-one and

Comparing kinetic profiles between bifunctional and binary type of Zn(salen)-based catalysts for organic carbonate formation

• Carmen Martín and
• Arjan W. Kleij

Beilstein J. Org. Chem. 2014, 10, 1817–1825, doi:10.3762/bjoc.10.191

•  1, Table S8 for more details). The carbonate product, 4-butyl-1,3-dioxolan-2-one, has been previously described, therefore its identification was done by comparison with reported data [52]. For a photograph of the reactor see Supporting Information File 1. Kinetic experiments For the catalytic

• [4-butyl-1,3-dioxolan-2-one]) and photographs of the reactor systems used for the catalytic/kinetic studies are given. Supporting Information File 486: Experimental procedures, typical 1H NMR spectra for aliquots taken in the kinetic studies and photographs of the reactor systems. Acknowledgements