Spectra Cover Sheet

Spectral  Data  for  

Aerobic  Alcohol  Oxidation  Using  a  CuI/TEMPO  Catalyst  System  

Nicholas J. Hill, Jessica M. Hoover and Shannon S. Stahl*

Department of Chemistry, University of Wisconsin-Madison,

1101 University Avenue, Madison, WI, 53706 stahl@chem.wisc.edu

Me

O

m/z = 120

H

Me

m/z = 119

+ resonance structures

O

Me

m/z = 91

Me

O

H

O

m/z = 148

H

O

H

O

m/z = 133

H

m/z = 119

O

m/z = 105

H

MeO

O

m/z = 136

H

MeO

O

H

MeO

m/z = 135

+ resonance structures

O

MeO

m/z = 107

Cl

O

m/z = 141 (37Cl)m/z = 139 (35Cl)+ resonance structures

Cl

O

H

m/z = 142 (37Cl)m/z = 140 (35Cl)

Cl

O

H

Br

O

m/z = 185 (81Br)m/z = 183 (79Br)+ resonance structures

Br

O

H

m/z = 186 (81Br)m/z = 184 (79Br)

m/z = 157 (81Br)m/z = 155 (79Br)

Br

Br

O

H

Me

OH

R = Me

m/z = 122

OH

m/z = 107

Me

m/z = 91

Cl

OH

R = Cl

m/z = 144 (37Cl)m/z = 142 (35Cl)

OH

m/z = 107

MeO

OH

R = OMe

m/z = 138

OH

m/z = 107

OH

R = iPr

m/z = 150

OH

m/z = 135 m/z = 119

Br

OH

R = Br

m/z = 188 (81Br)m/z = 186 (79Br)

OH

m/z = 107m/z = 157 (81Br)m/z = 155 (79Br)

Br

EI-Mass Spec Fragments of alcohols and aldehydes

Me

O

m/z = 120

Me m/z = 119+ resonance structures

HO

Cl

O

Cl

HO

m/z = 142 (37Cl)m/z = 140 (35Cl)

m/z = 141 (37Cl)m/z = 139 (35Cl)+ resonance structures

MeO

O

m/z = 136MeO

m/z = 135+ resonance structures

HO

O

m/z = 148

O

m/z = 133

O

m/z = 105

Br

O

Br

HO

m/z = 186 (81Br)m/z = 184 (79Br)

m/z = 185 (81Br)m/z = 183 (79Br)+ resonance structures

H H

H

MeO

m/z = 107