Derivatives of phenyl tribromomethyl sulfone as novel compounds with potential pesticidal activity

• Krzysztof M. Borys,
• Maciej D. Korzyński and
• Zbigniew Ochal

Beilstein J. Org. Chem. 2012, 8, 259–265, doi:10.3762/bjoc.8.27

• reducing agent. However, this method proceeded solely to debromination, and 4-dibromomethylsulfonyl-1,2-diamine (10) was isolated exclusively. Bromine cleavage in phenyl tribromomethyl sulfones was previously observed also by Fields and Shechter [13], who investigated the addition of phenyl tribromomethyl

• of the obtained compounds exhibit fungicidal activity. Retrosynthetic analysis of the designed target molecules. Synthetic routes for 4-chlorophenyl tribromomethyl sulfone (1). Halogenation/nitration sequence for 4-halogenphenyl methyl sulfones 4 and 4'. SNAr transformations of sulfone 6. Preparation

Synthesis and oxidation of some azole-containing thioethers

• Andrei S. Potapov,
• Nina P. Chernova,
• Vladimir D. Ogorodnikov,
• Tatiana V. Petrenko and
• Andrei I. Khlebnikov

Beilstein J. Org. Chem. 2011, 7, 1526–1532, doi:10.3762/bjoc.7.179

• through its conversion to sulfoxide or sulfone derivatives. In this report we present the synthesis of pyrazole and benzotriazole thioether ligands and their oxidation to the corresponding sulfoxides and sulfones. Results and Discussion 1-(2-Hydroxyethyl)-3,5-dimethylpyrazole (1), the starting compound

• oxidation reactions. Oxidation of thioethers to sulfoxides and sulfones can be achieved by using different oxidants and catalysts [15], hydrogen peroxide being the most versatile and green among them [16]. Despite the simplicity of their preparation and potentially useful properties, azole-containing

• sulfoxides and sulfones are not described in the literature. The action of one mole of hydrogen peroxide on thioether 3 in acetic acid at room temperature for 2.5 h selectively gives sulfoxide 6 (85% yield, Scheme 3). Raising the temperature to the boiling point of acetic acid (118 °C) and using an excess of

Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

• Abigail Page and
• Jonathan Clayden

Beilstein J. Org. Chem. 2011, 7, 1327–1333, doi:10.3762/bjoc.7.156

• ], sulfides and sulfones [13], and many of the methods we developed for their asymmetric synthesis employed dynamic resolution techniques under kinetic or thermodynamic control [6][11][13][14][15][16]. The mechanistic possibilities associated with dynamic resolution were initially elaborated by Beak for

The preparation of 3-substituted-1,5-dibromopentanes as precursors to heteracyclohexanes

• Bryan Ringstrand,
• Martin Oltmanns,
• Jeffrey A. Batt,
• Aleksandra Jankowiak,
• Richard P. Denicola and
• Piotr Kaszynski

Beilstein J. Org. Chem. 2011, 7, 386–393, doi:10.3762/bjoc.7.49

• been used as structural elements of liquid crystals [1][2][3][4][5][6] as well as antithrombotic and neuroprotectant agents [7][8]. Some thianes IV are found in petroleum distillates [9] and several have been used for the preparation of sulfones [7][10][11], sulfoxides [11][12], and sulfonium

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• other heavy metal fluorides, and even by silver tetrafluoroborate under mild conditions. The halex-method allows the selective preparation of α,α-difluoroalkyl aryl sulfides (and also ethers, sulfoxides and sulfones) as intermediate products in the synthesis of herbicides [66][67]. Interestingly, the

Recent advances in carbocupration of α-heterosubstituted alkynes

• Ahmad Basheer and
• Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

• pure sulfoxide was used as starting material, no racemization was detected [40]. 1-Alkynyl sulfones 38 are prone to addition of organocopper reagents. However, the stereochemistry of the resulting vinyl sulfones 39 appear to be dependent on the relative amounts of copper(I) bromide as well as the

• (toluene, reflux) and a single isomer was still obtained [53]. 1-Alkynyl sulfoximines behave similarly to alkynyl sulfones and the addition of an organocopper reagent usually leads to two isomers in variable amounts. Copper-catalyzed carbozincation to give a single regio- and stereoisomer in excellent

• -isomers. This effect can even be reinforced when an additional chelating unit is present (pyridylSi, phosphonates, sulfoxides, sulfones, sulfoximines). The resulting vinyl copper species can react with a large variety of electrophiles leading to functionalized adducts in a straightforward manner that can

Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine

• Jean Garnier,
• Alan R. Kennedy,
• Leonard E. A. Berlouis,
• Andrew T. Turner and
• John A. Murphy

Beilstein J. Org. Chem. 2010, 6, No. 73, doi:10.3762/bjoc.6.73

• , these two donors can also cleave appropriate arenesulfonamides [25], aryl alkyl sulfones [25][26], Weinreb amides [28] and acyloin derivatives [29]. They are also prone to transfer two electrons rather than one, with the cyclic voltammogram (c.v.) of 8 showing a single 2-electron reversible redox wave

The development and evaluation of a continuous flow process for the lipase- mediated oxidation of alkenes

• Charlotte Wiles,
• Marcus J. Hammond and
• Paul Watts

Beilstein J. Org. Chem. 2009, 5, No. 27, doi:10.3762/bjoc.5.27

• found widespread application in the conversion of nitriles to amides [32], aldehydes to acids [33], and sulfides to sulfones [34]. To enable comparison of the method developed here with batch investigations previously conducted, the oxidation of 1-methylcyclohexene (6) to 1-methylcyclohexene oxide (7

The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

• Shlomo Levinger,
• Ranjeet Nair and
• Alfred Hassner

Beilstein J. Org. Chem. 2008, 4, No. 32, doi:10.3762/bjoc.4.32

• series of α-sulfonylallylic donor precursors 1, bearing a remote stereogenic center, were prepared by condensing a chiral aryl- or heteroarylalkylamine 6 with the bromo-substituted allyl sulfone 5 [2] (Scheme 2 and Table 1). Of the primary amines 6 used for generation of amino-substituted sulfones 1, 1

• anthracene) is also worth noting in this context. Restricted rotation in acylnaphthalenes has been extensively studied [11]. Amino-substituted allyl sulfones 1 were deprotonated with LDA at −78 °C in THF and the lithio derivative obtained was allowed to react for a specified time at that temperature with

• atoms are omitted for clarity. Transmission of asymmetry in the conjugate addition of allyl sulfones to ethyl crotonate depending on the presence of a remote aromatic nucleus. Preparation of donor precursors for conjugate addition (1), bearing a remote stereogenic center. Borch reductive amination of

Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds

• G. K. Surya Prakash,
• Xiaoming Zhao,
• Sujith Chacko,
• Fang Wang,
• Habiba Vaghoo and
• George A. Olah

Beilstein J. Org. Chem. 2008, 4, No. 17, doi:10.3762/bjoc.4.17

• nucleophile to a variety of α,β-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. α-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to α,β-unsaturated ketones, esters, nitriles, sulfones, as well as

• and sulfones (Table 3). In case of α,β-unsaturated aldehydes the reaction was found to be not clean and too many fluorine peaks appeared in the 19F NMR even when the reaction was carried out at low temperatures. On the other hand, α,β-unsaturated nitriles underwent a second Michael addition of the

• course. Reaction mechanism for phosphine catalyzed 1,4-addition to α,β-unsaturated compounds. Oxidation of sulfides and monofluorination of sulfones. PMe3-catalyzed reaction of fluoro(phenylsulfonyl)-substituted methane derivatives with methyl vinyl ketone and ethyl acrylate. K2CO3/DMF catalyzed 1,4