Competing reactions of secondary alcohols with sodium hypochlorite promoted by phase-transfer catalysis.
With aqueous hypochlorite and a phase transfer catalyst, secondary alcohols undergo hitherto unreported free radical reactions that compete with and effectively limit traditional ketone syntheses. Product mixture profiles are determined by reactant ratios, organic cosolvent, and availability of oxygen to the system. Under argon, over half of substrate alcohols, PhCH(OH)R, are converted to benzaldehyde and free radical products through beta-scission of intermediate alkyl hypochlorites. Secondary alcohols with R containing three or more carbons also may undergo delta chlorination.
Bright
Zack R
ZR
Department of Chemistry, Texas Wesleyan University, Fort Worth, Texas 76105, and Department of Chemistry, University of Dallas, Irving, Texas 75060, USA.
Luyeye
Cedric R
CR
Morton
Angela Ste Marie
AS
Sedenko
Marina
M
Landolt
Robert G
RG
Bronzi
Matthew J
MJ
Bohovic
Katherine M
KM
Gonser
M W Alex
MW
Lapainis
Theodore E
TE
Hendrickson
William H
WH