Mayr's Database of Reactivity Parameters

Electrophiles

1 | 2 | 3 | 4 Found 355 molecules, displaying page 2 of 4 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
2,6-di-tert.butyl-4-(3-fluorobenzylidene)cyclohexa-2,5-dienone
C21H25FO*

E Param.: -15.03

***Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
1,2-diaza-1,3-diene 1c
*
DMSO

E Param.: -14.91

***Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1e
*
MeOH

E Param.: -14.90

*Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
3-nitro-1-tosyl-1H-indole
C15H12N2O4S*

E Param.: -14.87

***Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
4-methoxy-<i>trans-beta</i>-nitrostyrene
*

E Param.: -14.70

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
jul-indan-1,3-dione
C22H19NO2*

E Param.: -14.68

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
4-bromo-3-nitro-1-tosyl-1H-indole
C15H11BrN2O4S*

E Param.: -14.60

**Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
2-(4-methoxybenzylidene)-1,3-dithiane 1,1,3,3-tetraoxide
*
DMSO

E Param.: -14.55

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane
*

E Param.: -14.52

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
2,6-di-tert.butyl-4-(3,5-difluorobenzylidene)cyclohexa-2,5-dienone
C21H24F2O*

E Param.: -14.50

***Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 4-(dimethylamino)phenyl)
*

E Param.: -14.46

***Organometallics 2012, 31, 2416-2424
10.1021/om3000357
2,6-di-tert.butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-dienone
C21H25NO3*

E Param.: -14.36

***Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
4-methyl-<i>trans-beta</i>-nitrostyrene
*

E Param.: -14.23

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
(E)-tert-butyl benzylidenecarbamate (in DMSO)
C12H15NO2*
DMSO

E Param.: -14.22

***J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 3,5-difluorophenyl)
*

E Param.: -14.21

***Organometallics 2012, 31, 2416-2424
10.1021/om3000357
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = Ph)
*

E Param.: -14.14

***Organometallics 2012, 31, 2416-2424
10.1021/om3000357
ethyl 3-nitro-1H-indole-1-carboxylate
C11H10N2O4*

E Param.: -14.10

**Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
N-methyl maleimide
C5H7NO2*
DMSO

E Param.: -14.07

***Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
jul Meldrum's acid
C19H21NO4*

E Param.: -13.97

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
1,2-diaza-1,3-diene 1b
*
DMSO

E Param.: -13.90

***Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene
*
DMSO

E Param.: -13.88

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
<i>trans-beta</i>-nitrostyrene
*

E Param.: -13.85

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
julBBS
C19H21N3O3*

E Param.: -13.84

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
p-chloranil (C-Cl)
C6Cl4O2*

E Param.: -13.84

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane
*

E Param.: -13.77

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione
C18H15NO2*

E Param.: -13.56

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
N-methyl-N-((trifluoromethyl)thio)-p-toluenesulfonamide
*

E Param.: -13.44

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
dma(Ph)2QM
C27H23NO*

E Param.: -13.39

****Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
Umemoto I (tetrafluoroborate)
*

E Param.: -13.39

***Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
4-bromo-<i>trans-beta</i>-nitrostyrene
*

E Param.: -13.37

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
p-(dimethylamino)benzylidenemalononitrile
C12H11N3*

E Param.: -13.30

***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
1,2-diaza-1,3-diene 1a
*
DMSO

E Param.: -13.28

***Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,3,5-trinitrobenzene
C6H3N3O6*

E Param.: -13.19

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
Umemoto I (triflate)
*

E Param.: -13.08

***Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO)
C15H15NO3S*
DMSO

E Param.: -13.05

***J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
2-(4-methoxybenzylidene)benzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
DMSO

E Param.: -13.02

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
(2-phenylethene-1,1-diyldisulfonyl)dibenzene
*
DMSO

E Param.: -12.93

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
benzaldehyde (in DMSO)
C7H6O*
DMSO

E Param.: -12.90

*J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
3,6-dinitro-1-tosyl-1H-indole
*

E Param.: -12.90

***Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
Umemoto II (triflate)
*

E Param.: -12.80

***Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
dmaBBS
C15H17N3O3*

E Param.: -12.76

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
p-(dimethylamino)benzylidene Meldrum's acid
C15H17NO4*

E Param.: -12.76

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
4-cyano-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.61

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
N-(trifluoromethyl)thio)succinimide
*

E Param.: -12.56

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
4-nitro-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.37

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
2,4-dinitrothiophene
C4H2N2O4S*

E Param.: -12.33

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
2,5-dichloroquinone (C-H)
C6H2Cl2O2*

E Param.: -12.28

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
di-tert-butyl azodicarboxylate
*
MeCN

E Param.: -12.23

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
ani(Ph)2QM
C26H20O2*

E Param.: -12.18

****Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
p-chloranil (C=O)
C6Cl4O2*

E Param.: -12.13

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
ethenesulfonyl fluoride (ESF)
*
DMSO

E Param.: -12.09

***Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
o-chloranil (C-Cl)
C6Cl4O2*

E Param.: -12.02

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium
C21H21N2O3*
DMSO

E Param.: -12.02

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
N-(trifluoromethyl)thio)phthalimide
*

E Param.: -11.92

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
jul(S)BBS
C19H21N3O2S*

E Param.: -11.89

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone
C25H18O*

E Param.: -11.87

***Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
N-(difluoromethyl)thio)phthalimide
*

E Param.: -11.86

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium
C17H21N2O*
DMSO

E Param.: -11.80

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium
C20H19N2O2*
DMSO

E Param.: -11.79

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
DMSO

E Param.: -11.78

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one
C16H21F3O*
DMSO

E Param.: -11.68

***Eur. J. Org. Chem. 2020, , 3812-3817
10.1002/ejoc.202000295
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium
C14H15N2O*
DMSO

E Param.: -11.52

***Angew. Chem. Int. Ed. 2012, 51, 5234-5238
10.1002/anie.201109042
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)
C14H13NO2S*
DMSO

E Param.: -11.50

***J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium
C22H23N2O*
DMSO

E Param.: -11.48

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-(p-methoxybenzylidene)-indan-1,3-dione
C17H12O3*

E Param.: -11.32

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
maleic anhydride
C4H4O3*
DMSO

E Param.: -11.31

***Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,4-trichloro-1(2H)-naphthalenone
*
MeCN

E Param.: -11.24

***Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
dicarbonyl(cyclopentadienyl)propene-iron(II)
*

E Param.: -11.20

***Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
p-fluoranil (C-F)
C6F4O2*

E Param.: -11.12

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-(methoxy)benzylidenemalononitrile
C11H8N2O*

E Param.: -10.80

***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
dma(S)BBS
C15H17N3O2S*

E Param.: -10.73

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
diisopropyl azodicarboxylate
*
MeCN

E Param.: -10.71

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
p-AniCH=N+Me2 (in MeCN)
C10H14NO*
MeCN

E Param.: -10.69

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C24H30N3O*
dichloromethane

E Param.: -10.60

**Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
5,7,7-trichloro-8(7H)-quinolinone
*
MeCN

E Param.: -10.48

***Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate
*

E Param.: -10.46

***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
aniBBS
C14H14N2O4*

E Param.: -10.37

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
pipN+=CH-CH-Ph
C14H18N+*

E Param.: -10.30

*Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
p-(methoxy)benzylidene Meldrum's acid
C14H14O5*

E Param.: -10.28

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
bis(1,2-dimethylindol-3-yl)methylium ion
C21H21N2*

E Param.: -10.23

***J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
diethyl azodicarboxylate
*
MeCN

E Param.: -10.15

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
Pd-allyl cation
*

E Param.: -10.11

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-benzylidene-indan-1,3-dione
C16H10O2*

E Param.: -10.11

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium
C19H12F5N2O*
DMSO

E Param.: -10.09

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
(lil)2CH+
C23H25N2*

E Param.: -10.04

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-fluoropyridinium tetrafluoroborate
C5H5FN*

E Param.: -9.89

***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion
C27H32N3*

E Param.: -9.84

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
pyrN+=CH-CH-Ph
C13H16N+*

E Param.: -9.80

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
bis(julidin-9-yl)allylium ion
*

E Param.: -9.78

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
pTolCH=N+CH2 (in MeCN)
C10H14N*
MeCN

E Param.: -9.64

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)5 (in MeCN)
C12H16N*
MeCN

E Param.: -9.60

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
indolecarboxylate derived iminium ion
*
dichloromethane

E Param.: -9.50

**Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(jul)2CH+
C25H29N2*

E Param.: -9.45

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
benzylidenemalononitrile
C10H6N2*

E Param.: -9.42

***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-fluoranil (C=O)
C6F4O2*

E Param.: -9.37

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
PhCH=N+(CH2)4 (in MeCN)
C11H14N*
MeCN

E Param.: -9.35

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+Me2 (in MeCN)
C9H12N*
MeCN

E Param.: -9.27

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
C7H9+-Fe(CO)3
*

E Param.: -9.21

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c