Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants§

Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants§

2-(Dichloromethylidene)-1,1,3,3-tetramethylindane was “hydrolyzed” by solid KOH in DMSO as the solvent at ≥100 °C through an initial chlorine particle transfer to give a Cl,K-carbenoid. This short-lived intermediate disclosed its occurrence through a reversible proton transfer which competed with an...

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Bibliographic Details
Main Authors: Rudolf Knorr, Thomas Menke, Johannes Freudenreich, Claudio Pires
Format: Article
Language:English
Published: Beilstein-Institut 2014-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
brominative deoxygenation
carbenoid
DMSO
nucleophilic vinylic substitution
steric hindrance
Online Access:https://doi.org/10.3762/bjoc.10.28

Internet

https://doi.org/10.3762/bjoc.10.28

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