Conjugate addition of B-alkenyl-9-borabicyclo[3.3.1]nonanes to methyl vinyl ketone. A convenient synthesis of .gamma.,.delta.-unsaturated ketones

1976 ◽  
Vol 98 (24) ◽  
pp. 7832-7833 ◽  
Author(s):  
Peyton Jacob ◽  
Herbert Brown
Keyword(s):  
Conjugate Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Gamma Delta ◽  
Methyl Vinyl ◽  
Unsaturated Ketones ◽  
Convenient Synthesis

Aprotic Conjugate Addition Reactions of Lithiated Allylic Sulfoxides With Acyclic Enones; a Breakdown of the trans-Decalyl Transition State

1989 ◽  
Vol 42 (10) ◽  
pp. 1785 ◽  
Author(s):  
RK Haynes ◽  
AG Katsifis ◽  
LM King ◽  
SC Vonwiller
Keyword(s):  
Transition State ◽  
Conjugate Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Mesityl Oxide ◽  
Addition Reactions ◽  
State Characteristic ◽  
Methyl Vinyl ◽  
Cyclic Enones ◽  
Carbonyl Addition

The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.

scholarly journals Gas-phase selective conjugate addition of methanol to acetone for methyl vinyl ketone over SnO2 nanoparticle catalysts

2005 ◽  
Vol 16 (3b) ◽  
pp. 607-613 ◽  
Author(s):  
Humberto V. Fajardo ◽  
Luiz F. D. Probst ◽  
Antoninho Valentini ◽  
Neftalí L. V. Carreño ◽  
Adeilton P. Maciel ◽  
...  
Keyword(s):  
Gas Phase ◽  
Conjugate Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Methyl Vinyl ◽  
Nanoparticle Catalysts ◽  
Sno2 Nanoparticle

N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction

2000 ◽  
Vol 65 (5) ◽  
pp. 797-804 ◽  
Author(s):  
Martina Havelková ◽  
Martin Studenovský ◽  
Dalimil Dvořák
Keyword(s):  
Methyl Methacrylate ◽  
Butyl Acrylate ◽  
Heck Reaction ◽  
Conjugate Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Acetate Anion ◽  
Methyl Vinyl ◽  
Michael Acceptors

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alkylhypoxanthine derivatives. Formation of these unexpected products can be rationalised as a Tl+- or Ag+-assisted substitution of halogen with acetate anion. The 6-acetoxypurine derivative thus formed then eliminates ketene and gives 7-benzyl- or 9-benzylhypoxanthine. Conjugate addition of these compounds onto Michael acceptors furnishes the N1-substituted hypoxanthine derivatives.

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