58723-96-9Relevant academic research and scientific papers
Transition-Metal-Free One-Step Synthesis of Ynamides
Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
, p. 4458 - 4466 (2019/03/26)
A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
Hydrogen-Bonding-Assisted Br?nsted Acid and Gold Catalysis: Access to Both (E)- and (Z)-1,2-Haloalkenes via Hydrochlorination of Haloalkynes
Zeng, Xiaojun,Liu, Shiwen,Hammond, Gerald B.,Xu, Bo
, p. 904 - 909 (2018/02/14)
We have developed an efficient synthesis of both (Z)- and (E)-chlorohaloalkenes via hydrochlorination of haloalkynes, based on two distinct hydrogen-bond-network-assisted catalytic systems: Br?nsted acid catalysis and gold catalysis. Both systems offer high stereoselectivity, good chemical yields, and diverse functional group tolerance.
Preparation of (Z)-1,2-dichloroalkenes from terminal alkynes
Zhou, Ningzhang,Wang, Qiang,Lough, Alan J.,Yan, Hongbin
, p. 625 - 630 (2012/08/08)
(Z)-1,2-Dihaloalkenes are thermodynamically disfavoured of the two stereoisomers. This paper reports the synthesis of some (Z)-1,2-dichloroalkene analogues from mucochloric acid. A more versatile approach involved the chloroboration of terminal alkynes to yield corresponding (Z)-chloroboronic acid as a first step. Treatment of the organoboronic acid with potassium hydrogen difluoride followed by tetrabutylammonium trichloride gave (Z)-1,2- dichloroalkenes in moderate to good yields in a stereospecific manner.
Highly stereoselective synthesis of (Z)-1,2-dihaloalkenes by a Pd-catalyzed hydrohalogenation of alkynyl halides
Zhu, Gangguo,Chen, Dongxu,Wang, Yuyi,Zheng, Renwei
supporting information; experimental part, p. 5796 - 5798 (2012/07/28)
An unprecedented Pd-catalyzed hydrohalogenation of alkynyl halides for the regio- and stereoselective synthesis of (Z)-1,2-dihaloalkenes has been realized using [(allyl)PdCl]2 as the catalyst and cis,cis-1,5-cyclooctadiene as the ligand. The advantages of this protocol are well illustrated by the assembly of trisubstituted (Z)-enynes and multifunctional benzenes via iterative cross-coupling reactions or tandem Diels-Alder-aromatization reactions, respectively.
Quaternary ammonium polychlorides as efficient reagents for chlorination of unsaturated compounds
Zelikman,Tyurin,Smirnov,Zyk
, p. 1541 - 1546 (2007/10/03)
Chlorination of unsaturated compounds by benzyltributylammonium polychlorides results in higher yields of addition products compared to those obtained with molecular chlorine.
Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCI (HBr) Acetonitrile Reagent
Liu, Lilian Kao,Lin, Ching-Shan
, p. 61 - 66 (2007/10/03)
Addition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25-60 °C) with excellent to moderate yields.
INFLUENCE OF APROTIC SOLVENTS AND CHLORIDE ANIONS ON THE STEREOSELECTIVITY OF CHLORINATION OF PHENYLACETYLENE
Gutsulyak, R. B.,Britsun, V. N.,Serguchev, Yu. A.
, p. 426 - 429 (2007/10/02)
Chlorination of phenylacetylene in aprotic solvents was studied.The stereoselectivity of chlorine addition to a triple bond was found to depend on the chlorination mechanism.In aprotic solvents (CCl4, hexane, Freon-113) a significant contribution of radical process is observed, which gives rise to trans-addition of chlorine.Passing to the less polar (CHCl3) or aromatic (benzene, toluene, chlorobenzene) solvents and lowering the temperature to -60 deg C increase the contribution of molecular process and hence the yield of the cis-product.Additions of pyridinium chlorides result in selective formation of trans-product due to synchronous reaction of chlorine and chloride anion with the triple bond of phenylacetylene (donor-molecule-acceptor trimolecular principle).
Attempts to Prepare an Alkynyldiazonium Salt
Helwig, Reinhard,Hanack, Michael
, p. 1008 - 1021 (2007/10/02)
The 2-bromo-1-chloroalkanal p-tosylhydrazones 11a and b react with triethylamine as base to give the azoalkenes 12, of which (1-chloro-2-phenylethenyl)tosyldiazene (12b) is obtained as a crystalline material at room temperature. 12b reacts with SbCl5 at -30 and -70 deg C to form different diazonium salts, which are treated with nucleophiles such as methanol and water.The products obtained (Schemes 3 and 4) indicate the formation of the phenylethenyldiazonium salt 20, which is stable up to -20 deg C. 20 adds nucleophiles like methanol or water as well as anisole at the CC triple bond before releasing nitrogen.
ROLE OF THE POLYMER BACKBONE ON THE REACTIVITY OF POLYMER-SUPPORTED (DICHLOROIODO)BENZENE
Sket, Boris,Zupan, Marko,Zupet, Pavle
, p. 1603 - 1606 (2007/10/02)
Chlorination of iodinated crosslinked polystyrene with Cl2 gave polyaryliododichloride containing 1.1 mmol of active chlorine per gram of resin, while fluorination of the same iodinated resin with XeF2 gave polyaryliododifluoride, co
