112-19-6Relevant articles and documents
Epoxy-terminated self-assembled monolayers containing internal urea or amide groups
Ramin, Micha?l A.,Le Bourdon, Gwéna?lle,Heuzé, Karine,Degueil, Marie,Buffeteau, Thierry,Bennetau, Bernard,Vellutini, Luc
, p. 2783 - 2789 (2015)
We report the synthesis of new coupling agents with internal amide or urea groups possessing an epoxy-terminal group and trimethoxysilyl-anchoring group. The structural characterizations of the corresponding self-assembled monolayers (SAMs) were performed by polarization modulation infrared reflection adsorption spectroscopy (PM-IRRAS). The molecular assembly is mainly based on the intermolecular hydrogen-bonding between adjacent amide or urea groups in the monolayers. Because of the steric hindrance of amide or urea groups, the distance between the alkyl chains is too large to establish van der Waals interactions, inducing their disorder. The reactivity of the epoxy-terminal groups was successfully investigated through reaction with a fluorescent probe. We show that SAMs containing internal urea or amide groups exhibited a higher density of accessible epoxide groups than the corresponding long-chain (C22) glycidyl-terminated SAM.
Synthesis of methacrylate-functionalized phosphonates and phosphates with long alkyl-chain spacers and their self-aggregation in aqueous solutions
Francova, Denisa,Kickelbick, Guido
, p. 413 - 422 (2009)
Polymerizable amphiphilic organophosphorous compounds were synthesized and their self-aggregation behavior was investigated. The studied molecules contain a hydrophilic phosphorus end group, an alkyl chain spacer with a variable length from 3 to 11 CH2 groups and a polymerizable methacrylic group at the other chain end. Thus, the molecules represent a class of polymerizable surfactants. Two different reaction methods were used; either unsaturated alcohols or bromine-containing alcohols were applied as starting compounds for the preparation of the organophosphorous surfactants. The self-aggregation and micelle formation of the prepared compounds were investigated in aqueous solution by dynamic light scattering measurements. The critical micelle concentration of the P-containing amphiphiles was in all cases smaller than 0.040 mol/l and strongly dependent on the polarity of the phorphorous head group and the chain length of the spacer. Graphical abstract: [Figure not available: see fulltext.] The synthesis of organophosphorous amphiphiles as surface active monomers for the modification of metal oxide surfaces is presented. The spacer between the phosphorous head group and the methacrylate group was varied with regard to their length and composition. The self-aggregation behavior of these methacrylate-functionalized phosphates and phosphonates surfactants was investigated.
Reducing properties of 1,2-diaryl-1,2-disodiumethanes
Azzena, Ugo,Pittalis, Mario,Dettori, Giovanna,Madeddu, Simona,Azara, Emanuela
, p. 1055 - 1058 (2006)
1,2-Diphenyl- and 1-phenyl-2-(2-pyridyl)-1,2-disodiumethane efficiently dehalogenate vic-dibromoderivatives, affording the corresponding alkenes. The reaction proceeds rapidly, under mild conditions and is tolerant of a variety of functional groups (alcohol, carboxylic acid, ester and amide). This procedure was successfully extended to similar vic-disubstituted compounds.
A direct, straightforward conversion of methoxymethyl ethers into acetates
Bosch,Petschen,Guerrero
, p. 300 - 304 (2000)
The direct transformation of MOM-protected alcohols into the corresponding acetates by acetic anhydride/ferric chloride in CH2Cl2, in a one-step process and good to excellent yields, is reported. The reaction has been applied to a variety of substrates and occurs with retention of configuration.
Manganese-mediated acetylation of alcohols, phenols, thiols, and amines utilizing acetic anhydride
Jain, Isha,Sharma, Ramandeep,Malik, Payal
supporting information, p. 2952 - 2960 (2019/09/13)
Manganese(II) chloride-catalyzed acetylation of alcohols, phenols thiols and amines with acetic anhydride is reported. This method is environment-friendly and economically viable as it involves inexpensive, relatively benign catalyst, mild reaction condition, and simple workup. Acetylation is performed under the solvent-free condition at ambient temperature and acetylated products obtained in good to excellent yields. Primary, secondary heterocyclic amines, and phenols with various functional groups are smoothly acetylated in good yields. This method exhibits exquisite chemoselectivity, the amino group is preferentially acetylated in the presence of a hydroxyl/thiol group.
PRODUCTION OF AMINES VIA A HYDROAMINOALKYLATION REACTION
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Page/Page column 61, (2019/12/04)
Provided is a process for producing an amine via a hydroaminoalkylation reaction of a non-aromatic C-C double bond or C-C triple bond, said process comprising a step of reacting a compound comprising a non-aromatic C-C double bond or C-C triple bond with a reactive component which is obtainable by combining an aminal or a hemiaminal ether with an acidic medium comprising trifluoroacetic acid, wherein the aminal contains two amino groups independently selected from a secondary and a tertiary amino group that are linked by a methylene group wherein one hydrogen atom may be replaced by a further substituent, and at least one of the amino groups carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the hemiaminal ether contains a secondary or a tertiary amino group which carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the secondary or tertiary amino group is linked to an alkoxy group by a methylene group wherein one hydrogen atom may be replaced by a further substituent.
Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals
Du, Ya,Pearson, Ryan M.,Lim, Chern-Hooi,Sartor, Steven M.,Ryan, Matthew D.,Yang, Haishen,Damrauer, Niels H.,Miyake, Garret M.
supporting information, p. 10962 - 10968 (2017/08/22)
Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible-light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible-light PCs for trifluoromethylation reactions and dual photoredox/nickel-catalyzed C?N and C?S cross-coupling reactions, both of which have been historically exclusive to precious metal PCs.
