112-54-9Relevant articles and documents
Klass,D.L. et al.
, p. 3029 - 3034 (1963)
A useful and environmentally benign synthetic protocol for dethiolization by employing vanadium pentoxide catalyzed oxidation of ammonium bromide by hydrogen peroxide
Mondal, Ejabul,Bose, Gopal,Sahu, Priti Rani,Khan, Abu T.
, p. 1158 - 1159 (2001)
A wide variety of thioacetals and thioketals can be cleaved chemoselectively in presence of olefin and aromatic ring as well as other protecting groups to carbonyl compounds by employing V2O5 catalyzed oxidation of ammonium bromide by H2O2 in CH2Cl2-H2O solvent system; mild conditions, high selectivity, good yield, and no side products such as bromination or oxidation are some of the major advantages.
Halasz
, p. 297 (1953)
Dynamic Imine Chemistry at Complex Double Emulsion Interfaces
Zentner, Cassandra A.,Anson, Francesca,Thayumanavan,Swager, Timothy M.
, p. 18048 - 18055 (2019)
Interfacial chemistry provides an opportunity to control dynamic materials. By harnessing the dynamic covalent nature of imine bonds, emulsions are generated in situ, predictably manipulated, and ultimately destroyed along liquid-liquid and emulsion-solid interfaces through simple perturbation of the imine equilibria. We report the rapid production of surfactants and double emulsions through spontaneous in situ imine formation at the liquid-liquid interface of oil/water. Complex double emulsions with imine surfactants are stable to neutral and basic conditions and display dynamic behavior with acid-catalyzed hydrolysis and imine exchange. We demonstrate the potential of in situ imine surfactant formation to generate complex surfactants with biomolecules (i.e., antibodies) for biosensing applications. Furthermore, imine formation at the emulsion-solid interface offers a triggered payload release mechanism. Our results illustrate how simple, dynamic interfacial imine formation can translate changes in bonding to macroscopic outputs.
Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera: Lymantriidae)
Wakamura, Sadao,Arakaki, Norio,Yamamoto, Masanobu,Hiradate, Syuntaro,Yasui, Hiroe,Kinjo, Kunio,Yasuda, Tetsuya,Yamazawa, Hiroyuki,Ando, Tetsu
, p. 957 - 965 (2005)
Two distinct electroantennographycally active (EAG-active) components, A and B, and a weakly active component C were found in a solvent extract from virgin females of the Ishigaki strain of the tussock moth, Orgyia postica (Walker). Components A, B, and C were found in the extract of the females at 4.0, 0.5, and 4.0 ng/female respectively. Components A, B, and C were identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene [(11S,12S)-1: posticlure], (6Z)-henicos-6-en-11-one (2), and (6Z,9Z)-henicosa-6,9-diene (3), respectively. Component B was absent in the extract from the Okinawa strain, in which components A and C were present at 2.0 and 1.5 ng/female respectively. (11S,12S)-1 and the racemic mixture showed attractiveness for both the Okinawa and Ishigaki strains, whereas (11R,12R)-1 did not. The addition of 2 significantly reduced the trap catches with (11S,12S)-1 on the Okinawa strain which lacked 2, while there was no significant inhibitory effect on the Ishigaki strain. The addition of 3 to (11S,12S)-1 did not significantly affect trap catches at Ishigaki or Okinawa. This confirmed that the attractant pheromone of O. postica of the Ishigaki strain is also (11S,12S)-1.
Enolate and Other Carbon Nucleophile Alkylation Reactions Using 1,2-Cyclic Sulfates as Terminal Epoxide Equivalents
Hoye, Thomas R.,Crawford, Khushrav B.
, p. 520 - 522 (1994)
Enolates of esters and amides as well as α-sulfonyl-, α-cyano-, and α-phosphonyl-substituted anions react with cyclic sulfate 1 to give hydroxylated products arising from nucleophilic attack, on this terminal epoxide equivalent, at the primary carbon.
Pyridinium poly(hydrogen fluoride)-assisted cleavage of acetals and ketals
Watanabe, Yutaka,Kiyosawa, Youko,Tatsukawa, Akiko,Hayashi, Minoru
, p. 4641 - 4643 (2001)
Acetals, including ketals, were smoothly cleaved by the action of pyridinium poly(hydrogen fluoride) without addition of water or an alcohol in an anhydrous solvent.
Selective Production of Linear Aldehydes and Alcohols from Alkenes using Formic Acid as Syngas Surrogate
Chen, Junjun,Hua, Kaimin,Liu, Xiaofang,Deng, Yuchao,Wei, Baiyin,Wang, Hui,Sun, Yuhan
, p. 9919 - 9924 (2021/05/31)
Performing carbonylation without the use of carbon monoxide for high-value-added products is an attractive yet challenging topic in sustainable chemistry. Herein, effective methods for producing linear aldehydes or alcohols selectively with formic acid as both carbon monoxide and hydrogen source have been described. Linear-selective hydroformylation of alkenes proceeds smoothly with up to 88 % yield and >30 regioselectivity in the presence of single Rh catalyst. Strikingly, introducing Ru into the system, the dual Rh/Ru catalysts accomplish efficient and regioselective hydroxymethylation in one pot. The present processes utilizing formic acid as syngas surrogate operate simply under mild condition, which opens a sustainable way for production of linear aldehydes and alcohols without the need for gas cylinders and autoclaves. As formic acid can be readily produced via CO2 hydrogenation, the protocols represent indirect approaches for chemical valorization of CO2.
Cassis and Green Tea: Spontaneous Release of Natural Aroma Compounds from β-Alkylthioalkanones
B?ttig, Sarah,Egger, Timothy,Gey, Olga,Bochet, Christian G.,Flachsmann, Felix
, (2021/10/19)
In depth headspace analysis of the slow degradation of β-alkylthioalkanones in ambient air led to the discovery of a novel δ-cleavage pathway, by which β-mercaptoketones are released. Since β-mercaptoketones are potent natural aroma compounds occurring in many fruits, herbs and flowers, the discovery of an enzyme-independent molecular precursor for this class of high-impact molecules is of practical importance. Moreover, the formation of β-diketones and aldehydes by concomitant oxidation at the α-sulfur-position enhances the versatility of this class of aroma precursors. A mechanistic model is proposed which suggests that the oxidative degradation occurs through a novel Pummerer-type rearrangement of initially formed persulfoxides.
A Strategy for Accessing Aldehydes via Palladium-Catalyzed C?O/C?N Bond Cleavage in the Presence of Hydrosilanes
He, Zhanyu,Liu, Tingting,Ru, Junxiang,Wang, Yulin,Wang, Zijia,Zeng, Zhuo
supporting information, p. 5794 - 5800 (2020/12/01)
We report the catalytic reduction of both active esters and amides by selective C(acyl)?X (X=O, N) cleavage to access aldehyde functionality via a palladium-catalyzed strategy. Reactions are promoted by hydrosilanes as reducing reagents with good to excellent yields and with excellent chemoselectivity for C(acyl)?N and C(acyl)?O bond cleavage. Carboxylic acid C(acyl)?O bonds are activated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) to form triazine ester intermediates, which further react with hydrosilanes to yield aldehydes in one-pot two-step procedures. We demonstrate that C(acyl)?O cleavage/formylation offers higher yields and broader substrate scopes compared with C(acyl)?N cleavage under the same reaction conditions.