ChemInform Abstract: MODEL STUDIES OF THIAMINE CATALYSIS. COMPARISON OF THE EFFECTS OF HETEROATOMS AT ANNULAR POSITIONS ON SIDE-CHAIN KINETIC ACIDITY

1978 ◽  
Vol 9 (37) ◽  
Author(s):  
J. A. ZOLTEWICZ ◽  
J. K. O'HALLORAN
Keyword(s):  
Side Chain ◽  
Abstract Model ◽  
Model Studies ◽  
Kinetic Acidity

Experiments directed towards the synthesis of anthracyclinones. VII. Model studies with allyl naphthalenyl ethers

1983 ◽  
Vol 36 (4) ◽  
pp. 803 ◽  
Author(s):  
IK Boddy ◽  
RC Cambie ◽  
G Dixon ◽  
PS Rutledge ◽  
PD Woodgate
Keyword(s):  
Claisen Rearrangement ◽  
Side Chain ◽  
Model Studies ◽  
Chain Isomerization

The Claisen rearrangement of some allyl naphthalen-1-yl ethers has been examined, together with methods for modification of the resulting 2-ally1 side chain. Isomerization of the C-allyl substituent to a prop-1-enyl group followed by ozonolysis gives a formyl derivative, while ozonolysis of a 2-(2-methylprop-2-enyl) moiety or mercuriation of a 2-(2-chloroprop-2-enyl) substituent leads to an acetonyl derivative. Treatment of phenols with iodine(I) acetate and an excess of silver(I) acetate gives 4-hydroxyaryl acetates, probably via dienone intermediates.

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