Facile modification and fixation of diaryl disulphide-containing dynamic covalent polyesters by iodine-catalysed insertion-like addition reactions of styrene derivatives to disulphide units

2016 ◽  
Vol 7 (28) ◽  
pp. 4661-4666 ◽  
Author(s):  
Yukako Nakai ◽  
Akira Takahashi ◽  
Raita Goseki ◽  
Hideyuki Otsuka
Keyword(s):  
Addition Reactions ◽  
Styrene Derivatives

Insertion-like addition of disulphide-containing polyesters to styrene derivatives is reported, enabling facile control of various properties including dynamic covalent characteristics.

scholarly journals Preparation of Styrene Derivatives Containing Sulfide Group: Addition Reactions of Thiophenol and Its Derivatives to 1,4-Divinylbenzene

1990 ◽  
Vol 22 (11) ◽  
pp. 969-975 ◽  
Author(s):  
Eiichi Kobayashi ◽  
Jian Jiang ◽  
Hiroyoshi Matsumoto ◽  
Junji Furukawa
Keyword(s):  
Addition Reactions ◽  
Styrene Derivatives ◽  
Sulfide Group

scholarly journals Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

2015 ◽  
Vol 11 ◽  
pp. 1226-1234 ◽  
Author(s):  
Gerold Heuger ◽  
Richard Göttlich
Keyword(s):  
Addition Reactions ◽  
Redox Catalysis ◽  
Double Bonds ◽  
Concerted Mechanism ◽  
Unsaturated Compounds ◽  
Excellent Yield ◽  
Styrene Derivatives ◽  
Polar Mechanism

N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry.

Synthesis of β-Phenethyl Ethers by Base-Catalyzed Alcohol Addition Reactions to Aryl Alkenes

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2218-2224 ◽  
Author(s):  
Jeffrey Bandar ◽  
Chaosheng Luo
Keyword(s):  
Addition Reaction ◽  
Bioactive Molecules ◽  
Addition Reactions ◽  
Catalytic Transformation ◽  
Future Directions ◽  
Recent Approach ◽  
Potential Applications ◽  
Styrene Derivatives ◽  
Markovnikov Addition ◽  
Ether Synthesis

The direct anti-Markovnikov addition of alcohols to styrene derivatives represents a streamlined route to β-phenethyl ethers, a substructure frequently found in pharmaceuticals and other bioactive ­molecules. Here, we discuss how the development of such a reaction can complement and address limitations of current methods for β-phenethyl ether synthesis. In particular, we highlight our recent ­approach toward achieving this challenging alcohol addition reaction through P4-t-Bu superbase catalysis. A summary of compatible aryl alkenes and alcohols is provided to inform readers of potential applications of this new catalytic transformation, as well as its current limitations and future directions.1 Introduction2 Anti-Markovnikov Alcohol Addition to Aryl Alkenes: Background3 Superbase-Catalyzed Alcohol Addition to Aryl Alkenes4 Summary and Outlook

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

2019 ◽  
Author(s):  
Benjamin Lipp ◽  
Lisa Marie Kammer ◽  
Murat Kucukdisli ◽  
Adriana Luque ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Formation ◽  
Three Component Reaction ◽  
Broad Variety ◽  
Styrene Derivatives ◽  
Mechanistic Investigations

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox-catalyzed three-component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination.<br>

Thia-Michael Addition Reactions in Water Using 3-[Bis(Alkylthio) Methylene] Pentane-2,4-Diones as Odorless and Efficient Thiol Equivalents

2007 ◽  
Vol 4 (4) ◽  
pp. 281-284 ◽  
Author(s):  
Yanyan Chai ◽  
Dewen Dong ◽  
Yan Ouyang ◽  
Yongjiu Liang ◽  
Yan Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reactions

Ionic dimerisation of trifluoropropenenitrile and its addition reactions with methyl trifluoropropenoate

1980 ◽  
Vol 45 (2) ◽  
pp. 406-414 ◽  
Author(s):  
Jiří Svoboda ◽  
Oldřich Paleta ◽  
Václav Dědek
Keyword(s):  
Reaction Mechanism ◽  
Proton Transfer ◽  
Substituent Effect ◽  
Solvent Molecule ◽  
Addition Product ◽  
Potassium Fluoride ◽  
Relative Reactivity ◽  
Addition Reactions ◽  
Tertiary Amines ◽  
Optimum Conditions

Dimerisation of trifluoropropenenitrile (I) in the presence of potassium fluoride and tertiary amines afforded a mixture of stereoisomeric perfluoro-4-methyl-pentenedinitriles (II), higher-boiling compounds, and 2,3,3,3-tetrafluoropropanenitrile (III) which arises by proton transfer from the solvent molecule. Under optimum conditions, product II was obtained in about 50% yield. Reaction of the nitrile I with methyl trifluoropropenoate (IV) gave, besides the dimers II and V, the product of addition of the nitrile I to the propenoate, IV, i.e. methyl 4-cyanoperfluoro-2-pentenoate (VI), and the addition product of the propenoate IV to the nitrile I, i.e. methyl 4-cyanoperfluoro-2-methyl-3-butenoate (VII). The relative reactivity if I and IV is discussed. The ratio of stereoisomers in II, V, VI and VII indicates that the magnitude of the steric substituent effect, operating in the reaction mechanism, decreases in the order -CFCF3.(COOCH3) > -CFCF3(CN) > -COOCH3 > -CN.

[OsH4(PPh3)3]: New Catalyst for the Selective Cyclopropanation of Activated Olefins

1996 ◽  
Vol 61 (12) ◽  
pp. 1798-1804 ◽  
Author(s):  
Albert Demonceau ◽  
François Simal ◽  
Corine A. Lemoine ◽  
Alfred F. Noels ◽  
Igor T. Chizhevsky ◽  
...  
Keyword(s):  
Title Compound ◽  
Efficient Catalyst ◽  
Ethyl Diazoacetate ◽  
Styrene Derivatives ◽  
Activated Olefins ◽  
Cyclic Alkenes

The title compound was found to be an efficient catalyst for the selective cyclopropanation of activated olefins by ethyl diazoacetate. The cyclopropane yields range from moderate to good (75 to 95%) for activated olefins such as styrene and styrene derivatives, but are rather low (20 to 30%) for non-activated olefins such as terminal and cyclic alkenes. In the intermolecular competition, styrene was 45 times more reactive than cyclooctene. In all cases, trans (exo) cyclopropane predominated over the cis (endo) isomer.

Relative Reactivities of 1,1,1-Trichloroethane and 1,1,1-Trichlorotrifluoroethane in Competitive Addition Reactions

1992 ◽  
Vol 57 (6) ◽  
pp. 1291-1298 ◽  
Author(s):  
František Adámek ◽  
Milan Hájek ◽  
Zbyněk Janoušek
Keyword(s):  
Free Radical ◽  
Reaction Mechanism ◽  
Relative Reactivity ◽  
Addition Reactions ◽  
Radical Initiation ◽  
Amine Complexes ◽  
Free Radical Initiation ◽  
Ru Complexes ◽  
Radical Initiators

Relative reactivity of CH3CCl3 and CF3CCl3 measured in competitive addition reactions with 1-hexene in the presence of free radical initiators or Cu, Pd and Ru complexes was found to depend on the type of catalyst. The unusual course of the reaction has been found in the additions catalyzed with copper(I)-amine complexes where CH3CCl3 in competition with CF3CCl3 was completely unreactive. The results have been explained in terms of the change of reaction mechanism and compared with classical free radical initiation.

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