Organoselenium-Catalyzed Oxidative Ring Expansion of Methylenecyclopropanes with Hydrogen Peroxide

ChemCatChem ◽  
2016 ◽  
Vol 8 (6) ◽  
pp. 1033-1037 ◽  
Author(s):  
Lei Yu ◽  
Fenglin Chen ◽  
Yuanhua Ding
Keyword(s):  
Hydrogen Peroxide ◽  
Ring Expansion ◽  
Oxidative Ring Expansion

scholarly journals Lipase-Induced Oxidative Furan Rearrangements

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1293-1296 ◽  
Author(s):  
Jan Deska ◽  
Fabian Blume ◽  
Petra Sprengart
Keyword(s):  
Hydrogen Peroxide ◽  
Ring Expansion ◽  
Candida Antarctica ◽  
Lipase B ◽  
Aqueous Hydrogen Peroxide ◽  
Mild Conditions ◽  
Oxidative Ring Expansion

Lipase B from Candida antarctica catalyzes the oxidative ring expansion of furfuryl alcohols using aqueous hydrogen peroxide to yield functionalized pyranones under mild conditions. The method further allows for the preparation of corresponding piperidinone derivatives by enzymatic rearrangement of N-protected furfurylamines.

Acid-catalyzed rearrangement of hydroperoxides. II. Phenylcycloalkyl hydroperoxides

1968 ◽  
Vol 46 (9) ◽  
pp. 1561-1570 ◽  
Author(s):  
Glenn H. Anderson ◽  
James G. Smith
Keyword(s):  
Hydrogen Peroxide ◽  
Ferrous Sulfate ◽  
Phenyl Group ◽  
Ring Expansion ◽  
Steric Interaction ◽  
Ring Strain ◽  
Mineral Acids ◽  
Acid Catalyzed

The acid-catalyzed rearrangement of 1-phenylcycloalkyl hydroperoxides has been investigated using the cyclohexyl, cyclopentyl, and cyclobutyl compounds. Evidence was sought for rearrangement of the cycloalkyl group in competition with migration of the phenyl group during the reaction. Such a rearrangement would result in ring expansion of the cycloalkyl group to give, ultimately, products formed by cycloalkyl ring opening.No evidence for such a reaction was found in the case of 1-phenylcyclohexyl hydroperoxide; only the expected products, phenol and cyclohexanone, were detected. However, rearrangement of 1-phenylcyclopentyl hydroperoxide gave, besides the expected phenol and cyclopentanone, significant amounts of the ring-opened compound 4-hydroxyvalerophenone as its acetate. A second product, 1-phenylcyclopentene, arose by elimination of hydrogen peroxide from the hydroperoxide.1-Phenylcyclobutyl hydroperoxide proved to undergo ring expansion with great facility. Only the ring expanded products, 2-phenyl-2-tetrahydrofuryl hydroperoxide and its corresponding peroxide, could be isolated in the treatment of 1-phenylcyclobutanol with hydrogen peroxide using catalytic amounts of mineral acids. However, in the absence of catalysts, 1-phenylcyclobutyl hydroperoxide was formed in detectable amounts and its presence was demonstrated by decomposition with ferrous sulfate to butyro-phenone and 1,6-dibenzoylhexane.It seems reasonable that ring strain is the factor promoting the ring expansion of 1-phenylcyclobutyl hydroperoxide. In the case of 1-phenylcyclopentyl hydroperoxide, it is suggested that the steric interaction of the ortho hydrogens of the phenyl group with the cyclopentyl ring protons has the effect of slowing the migration of the phenyl group sufficiently that alkyl migration can occur to give the observed ring-opened products.

The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

1998 ◽  
Vol 39 (8) ◽  
pp. 881-884 ◽  
Author(s):  
Christopher D. Gabbutt ◽  
John D. Hepworth ◽  
B. Mark Heron ◽  
Jean-Luc Thomas
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

Oxidative ring-expansion of benzothiazolines into 1,4-benzothiazines

1981 ◽  
Vol 18 (2) ◽  
pp. 279-282 ◽  
Author(s):  
Gaetano Liso ◽  
Giuseppe Trapani ◽  
Andrea Latrofa ◽  
Paolo Marchini
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furylsulfonamides and N→O Sulfonyl Transfer.

ChemInform ◽  
2007 ◽  
Vol 38 (34) ◽  
Author(s):  
Robert Hodgson ◽  
Andrew Kennedy ◽  
Adam Nelson ◽  
Alexis Perry
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion
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