Synthesis of C1-C6 Segment of Carbonolide B: Wolff Rearrangement of Sugar α-Diazo Ketones

Synthesis ◽  
2000 ◽  
Vol 2000 (03) ◽  
pp. 395-398 ◽  
Author(s):  
Jayant N. Tilekar ◽  
Nitin T. Patil ◽  
Dilip D. Dhavale
Keyword(s):  
Wolff Rearrangement ◽  
Carbonolide B

ChemInform Abstract: Synthesis of C1-C6 Segment of Carbonolide B: Wolff Rearrangement of Sugar α-Diazo Ketones.

ChemInform ◽  
2010 ◽  
Vol 31 (25) ◽  
pp. no-no
Author(s):  
Jayant N. Tilekar ◽  
Nitin T. Patil ◽  
Dilip D. Dhavale
Keyword(s):  
Wolff Rearrangement ◽  
Carbonolide B

An unusual abnormal Wolff rearrangement

2003 ◽  
Vol 81 (6) ◽  
pp. 517-524 ◽  
Author(s):  
Howard E Zimmerman ◽  
Pengfei Wang
Keyword(s):  
Reaction Mechanism ◽  
Ab Initio ◽  
Transition Structure ◽  
Wolff Rearrangement ◽  
Photochemical Rearrangement ◽  
Bicyclic Structure

An unusual example of the abnormal Wolff rearrangement was studied. The bicyclic structure of the reactant and intermediates precluded some mechanistic possibilities of this unusual Abnormal Wolff Rearrangement. The study involved the photochemical rearrangement of diazodehydronorbornone bearing phenyl and 2-pyridyl groups at C-7. A number of examples of interesting stereoselectivity were encountered. The mechanism was investigated by use of ab initio QST type computations which located a unique transition structure species accounting for the reaction mechanism.Key words: abnormal-Wolff, carbene, rearrangement, QM computations, reaction mechanism.

Wolff rearrangement of (1-diazo-2-oxoalkyl) silanes

Tetrahedron ◽  
1989 ◽  
Vol 45 (17) ◽  
pp. 5517-5530 ◽  
Author(s):  
Ralf Brückmann ◽  
Klaus Schneider ◽  
Gerhard Maas
Keyword(s):  
Wolff Rearrangement
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