Metal-oxide induced redox chain addition of tetrachloromethane to a carbon-carbon double bond

1980 ◽  
Vol 45 (12) ◽  
pp. 3488-3501 ◽  
Author(s):  
Milan Hájek ◽  
Přemysl Šilhavý ◽  
Jaroslav Málek
Keyword(s):  
Double Bond ◽  
Metal Oxide ◽  
Addition Reaction ◽  
Carbon Double Bond ◽  
Redox Chain

Formation of 1 : 1 adducts in the addition of tetrachloromethane to a terminal carbon-carbon double bond was investigated at 76-200 °C. The redox chain addition reaction with 1-octene, electron-deficient alkenes and unconjugated aliphatic dienes induced by catalytic amounts of copper(I) or copper(II) oxides in conjugation with diethylamine or diisopropylamine afforded the corresponding 1 : 1 adducts up to in 85% yields. Aliphatic 1,3-dienes underwent redox chain 1,4-addition giving isomeric 1,1,1,5-tetrachloro-3-alkenes.

An investigation of the photodecomposition of N-bromosuccinimide; the generation and reactivity of succinimidyl radical

1979 ◽  
Vol 57 (15) ◽  
pp. 1967-1976 ◽  
Author(s):  
Fu-Lung Lu ◽  
Yousry M. A. Naguib ◽  
Masayuki Kitadani ◽  
Yuan L. Chow
Keyword(s):  
Double Bond ◽  
Low Temperature ◽  
Ethylene Oxide ◽  
Addition Reaction ◽  
Bromine Atom ◽  
Electronic Configuration ◽  
High Concentration ◽  
Carbon Double Bond ◽  
Acetonitrile Solutions

The photolysis of acetonitrile solutions of N-bromosuccinimide (NBS) in the presence of ethylene oxide and an excess of olefins or benzene in the −30 ∼ 20 °C range was shown to generate the succinimidyl radical in competition with the bromine atom reactions. The succinimidyl radical preferentially attacked a π bond to give 1-succinimidyl-2-bromoalkanes, rather than abstracting alkyl hydrogens. Allylic bromination also occurred and competed with the 1,2-addition. Formation of 3-bromocyclohexene in the presence of cyclohexene at 10–20 °C could be effectively reduced at lower temperatures or in the presence of a high concentration of ethylene oxide; the 1,2-addition process was favored at low temperature but surprisingly not facilitated significantly in the presence of ethylene oxide. The primary adducts from benzene readily eliminate HBr to give N-phenylsuccinimide. The attack of a bromine atom on a carbon–carbon double bond may become an important step in the 0 ∼ −30 °C range. The ease of the addition reaction suggests that this succinimidyl radical may have a Σ electronic configuration.

Energetics oftert-Butoxyl Addition Reaction to Norbornadiene: A Method for Estimating the π-Bond Strength of a Carbon−Carbon Double Bond

2009 ◽  
Vol 113 (23) ◽  
pp. 6524-6530 ◽  
Author(s):  
Paulo M. Nunes ◽  
Sílvia G. Estácio ◽  
Gustavo T. Lopes ◽  
Filipe Agapito ◽  
Rui C. Santos ◽  
...  
Keyword(s):  
Double Bond ◽  
Bond Strength ◽  
Addition Reaction ◽  
Carbon Double Bond

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

Cycloaddition reactions across the carbon-carbon double bond of thiirene 1,1-dioxide

1984 ◽  
Vol 49 (7) ◽  
pp. 1300-1302 ◽  
Author(s):  
Mitsuo Komatsu ◽  
Yasuo Yoshida ◽  
Masatoshi Uesaka ◽  
Yoshiki Ohshiro ◽  
Toshio Agawa
Keyword(s):  
Double Bond ◽  
Cycloaddition Reactions ◽  
Carbon Double Bond

ChemInform Abstract: Electrooxidative Fission of Carbon-Carbon Double Bond in a K2OsO2(OH)4/ HIO4 Double Mediatory System.

ChemInform ◽  
2010 ◽  
Vol 27 (5) ◽  
pp. no-no
Author(s):  
H. TANAKA ◽  
R. KIKUCHI ◽  
M. BABA ◽  
S. TORII
Keyword(s):  
Double Bond ◽  
Carbon Double Bond

Unusual carboncarbon double bond cleavage in thiophenohomotropone system promoted by ethanedithiol

1982 ◽  
Vol 23 (28) ◽  
pp. 2859-2862 ◽  
Author(s):  
Bernard Hanquet ◽  
Mohammed El Borai ◽  
Roger Guilard ◽  
Yves Dusausoy
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Carbon Double Bond

Raman Spectra of Polyisoprene Rubbers

1970 ◽  
Vol 43 (2) ◽  
pp. 313-321 ◽  
Author(s):  
S. W. Cornell ◽  
J. L. Koenig
Keyword(s):  
Double Bond ◽  
Raman Spectra ◽  
Structure Type ◽  
Peak Height ◽  
Mixed Structure ◽  
Carbon Double Bond

Abstract The Raman spectra of cis-1,4-, trans-1,4-, and 3,4-polyisoprene are presented, and the frequencies are classified by configurational structure type. The stretching frequency of the carbon-carbon double bond vibrations are used to describe structure content. Only Raman bands characteristic of total 1,4 content and total vinyl content can be observed. Tentative values of structure content determined by both peak height and peak area are presented for two mixed structure rubbers.

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