ChemInform Abstract: INTRAMOLECULAR FREE RADICAL FUNCTIONALIZATION OF THE METHYL GROUP OF 5′-DEOXYADENOSINE

1982 ◽  
Vol 13 (11) ◽  
Author(s):  
D. GANI ◽  
A. W. JOHNSON ◽  
M. F. LAPPERT
Keyword(s):  
Free Radical ◽  
Methyl Group ◽  
Radical Functionalization

The α-alkoxycarbonylation of saturated carbonyl compounds. The synthesis of 17α-hydroxymethyl 20-keto steroids

1978 ◽  
Vol 56 (3) ◽  
pp. 410-418 ◽  
Author(s):  
D. Mukherjee ◽  
CH. R. Engel
Keyword(s):  
Free Radical ◽  
Carbonyl Compounds ◽  
Keto Group ◽  
Methyl Group ◽  
Lithium Enolates ◽  
Enol Acetates ◽  
Radical Functionalization

It is shown that enolate ions, in particular lithium enolates obtained from enol acetates of saturated ketones by reaction with methyllithium, may not only be alkylated and carboxylated, but also alkoxycarbonylated (in position a to the original saturated keto group). By this method, saturated 20-keto steroids were transformed into 17α-methoxycarbonyl 20-ketones. Thus, from pregnenolone, 17-methoxycarbonylpregnenolone was prepared and was then converted to 17-hydroxymethylprogesterone and to some of its esters. This method for preparing 17-hydroxymethylated hormone analogues of the progesterone-corticoid group is simpler and more efficient than the pathway implying a free-radical functionalization of a 17α-methyl group.

scholarly journals 3-[1-(4-Bromophenyl)ethoxy]-2,2,5-trimethyl-4-phenyl-3-azahexane

2013 ◽  
Vol 69 (12) ◽  
pp. o1792-o1793
Author(s):  
Praveen Pitliya ◽  
Ray J. Butcher ◽  
A. Karim ◽  
Paul F. Hudrlik ◽  
Anne M. Hudrlik ◽  
...  
Keyword(s):  
Free Radical ◽  
Dihedral Angle ◽  
Torsion Angle ◽  
Title Compound ◽  
Ethoxy Group ◽  
Methyl Group ◽  
X Ray ◽  
Compound C ◽  
Butyl Group ◽  
Benzene Rings

The title compound, C22H30BrNO, is an alkoxyamine compound, an effective initiator in nitroxide-mediated free radical polymerization. It was prepared as a mixture of two diasteromers; the crystal for the X-ray analysis showed one of these as a pair ofR,SandS,Renantiomers. Thetert-butyl and isopropyl groups are in an almostanticonformation in the crystal [C—N—C—C torsion angle = −168.8 (1)°], and the methyl group of the ethoxy group is in an approximateantirelationship to thetert-butyl group. The dihedral angle between the phenyl and benzene rings is 33.12 (7)°. The Br atom is disordered over two positions, with occupancies of 0.9139 (16) and 0.0861 (16). In the crystal, weak C—H...Br contacts link the molecules into chains along [-110].

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