Photochemistry of o-benzyloxyphenylglyoxylates. A case of favored intramolecular hydrogen abstraction via a seven-membered cyclic transition state

1970 ◽  
Vol 92 (23) ◽  
pp. 6927-6931 ◽  
Author(s):  
Socrates P. Pappas ◽  
James E. Alexander ◽  
Robert D. Zehr
1972 ◽  
Vol 50 (6) ◽  
pp. 706-709 ◽  
Author(s):  
L. Tan ◽  
H. M. Wang ◽  
P. Falardeau

The fragmentation of 17α-hydroperoxypregnenolone and 17α-hydroperoxyprogesterone by electron impact and thermolysis is described. It is shown that the fragmentation pattern follows a common pathway for both compounds, determined exclusively by the substituents at ring-D. A new reaction in steroid chemistry, termed deoxygenation, is discovered and its mechanism explained by intramolecular hydrogen abstraction via a six-membered cyclic transition state involving the 20-ketone group.


1983 ◽  
Vol 24 (42) ◽  
pp. 4621-4624 ◽  
Author(s):  
Cosme G Francisco ◽  
Raimundo Freire ◽  
Rosendo Hernández ◽  
Maria C Medina ◽  
Ernesto Suárez

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