A new preparative ring expansion for bicyclic ketones. Homoketonization of cyclopropoxide analogs

1980 ◽  
Vol 58 (23) ◽  
pp. 2730-2732 ◽  
Author(s):  
Yumiko Hoyano ◽  
Vijay Patel ◽  
J. B. Stothers
Keyword(s):  
Ring Expansion ◽  
Synthetic Method ◽  
Ring Systems ◽  
Bicyclic Ketones

Homoketonization of some readily prepared cyclopropoxides affords a new synthetic method for ring expansion of the [2.2.1] and [2.2.2] ring systems.

13C magnetic resonance studies. 124. Preparative ring expansions of bicyclic ketones by homoketonization of cyclopropoxide analogs

1986 ◽  
Vol 64 (7) ◽  
pp. 1390-1399 ◽  
Author(s):  
Vijay Patel ◽  
Arthur J. Ragauskas ◽  
J. B. Stothers
Keyword(s):  
Magnetic Resonance ◽  
Ring Expansion ◽  
Synthetic Method ◽  
Expansion Process ◽  
Enol Ethers ◽  
Magnetic Resonance Studies ◽  
Silyl Ethers ◽  
Silyl Enol Ethers ◽  
Ring Expansions ◽  
Bicyclic Ketones

Homoketonization of some readily prepared cyclopropoxides provides a new synthetic method for ring expansion of the [2.2.1] and [2.2.2] ring systems. Cyclopropanation of the trimethylsilyl enol ethers derived from a variety of polycyclic ketones affords the required cyclopropyl silyl ethers, which may be ketonized directly or hydrolyzed to the corresponding cyclopropanols before ketonization. The results for fourteen examples serve to define the scope of the ring expansion process, and the silyl enol ethers, cyclopropyl silyl ethers, and most of the corresponding cyclopropanols have been characterized by 13Cmr. The stereochemistry of the ketonization leading to ring expansion has been established by deuterium labelling experiments.

A Novel Synthetic Method of Bicyclic Pyrans via the Palladium-Catalyzed Tandem­ Cyclization/Ring Expansion between Enynals and Dimethyl Acetyl­enedicarboxylate

Synthesis ◽  
2004 ◽  
Vol 2004 (09) ◽  
pp. 1409-1412 ◽  
Author(s):  
Naoki Asao ◽  
Yoshinori Yamamoto ◽  
Kenichiro Sato ◽  
Salprima Yudha S.
Keyword(s):  
Ring Expansion ◽  
Synthetic Method ◽  
Palladium Catalyzed

ChemInform Abstract: Regio- and Stereochemical Course of the Ring Expansion of Bridged Bicyclic Ketones to Spirocyclic α-Keto Tetrahydrofurans.

ChemInform ◽  
1992 ◽  
Vol 23 (51) ◽  
pp. no-no
Author(s):  
L. A. PAQUETTE ◽  
J. F. P. ANDREWS ◽  
C. VANUCCI ◽  
D. E. LAWHORN ◽  
J. T. NEGRI ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Bicyclic Ketones

Regio- and stereochemical course of the ring expansion of bridged bicyclic ketones to spirocyclic .alpha.-keto tetrahydrofurans.

1992 ◽  
Vol 57 (14) ◽  
pp. 3956-3965 ◽  
Author(s):  
Leo A. Paquette ◽  
John F. P. Andrews ◽  
Corinne Vanucci ◽  
David E. Lawhorn ◽  
Joanna T. Negri ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Bicyclic Ketones
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