Structural requirements for the photochemical ring expansion of cyclic ketones to cyclic acetals

1975 ◽  
pp. 737 ◽  
Author(s):  
Peter Yates ◽  
Janet C. L. Tam
Keyword(s):  
Ring Expansion ◽  
Cyclic Ketones ◽  
Structural Requirements ◽  
Cyclic Acetals

Migratory selectivity in the ring expansion of .alpha.,.beta.-unsaturated cyclic ketones via .beta.-hydroxy selenides

1985 ◽  
Vol 50 (25) ◽  
pp. 5200-5204 ◽  
Author(s):  
Leo A. Paquette ◽  
John R. Peterson ◽  
Robert J. Ross
Keyword(s):  
Ring Expansion ◽  
Cyclic Ketones ◽  
Alpha Beta

α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau–Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 373-377
Author(s):  
Mikhail Krasavin ◽  
Sergey Chuprun ◽  
Dmitry Dar’in ◽  
Grigory Kantin ◽  
Petr Zhmurov
Keyword(s):  
Ring Expansion ◽  
Cyclic Ketones ◽  
Lawesson’S Reagent ◽  
Lawesson's Reagent

A novel Sc(OTf)3-catalyzed Tiffeneau–Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson’s reagent.

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