1.5-Dienes from allylic alcohols and carbonyl compounds by successive Claisen rearrangement, Wittig reaction, and Cope rearrangement: an attempted synthesis of ‘propylure’

1973 ◽  
pp. 2738-2741 ◽  
Author(s):  
Richard C. Cookson ◽  
Norman W. Hughes
Keyword(s):  
Carbonyl Compounds ◽  
Wittig Reaction ◽  
Claisen Rearrangement ◽  
Allylic Alcohols ◽  
Cope Rearrangement

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

Syntheses of trifluoromethylated diene derivatives through the claisen rearrangement of trifluoromethylated propargylic and allylic alcohols

1985 ◽  
Vol 26 (2) ◽  
pp. 219-222 ◽  
Author(s):  
Yuji Hanzawa ◽  
Kei-ichi Kawagoe ◽  
Akio Yamada ◽  
Yoshiro Kobayashi
Keyword(s):  
Claisen Rearrangement ◽  
Allylic Alcohols

Formation of α,β-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols

1994 ◽  
Vol 35 (38) ◽  
pp. 7097-7098 ◽  
Author(s):  
Enrique Gómez-Bengoa ◽  
Pedro Noheda ◽  
Antonio M. Echavarren
Keyword(s):  
Carbonyl Compounds ◽  
Allylic Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation
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