Mayr's Database of Reactivity Parameters

Other Michael acceptors

For reactivities of structurally related compounds go to: Electrophiles » C-Electrophiles » Acceptor-Substituted Ethylenes » Other Michael acceptors

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
benzylidenemalononitrile
C10H6N2 *

E Param.: -9.42

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-(methoxy)benzylidenemalononitrile
C11H8N2O *

E Param.: -10.80

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-(dimethylamino)benzylidenemalononitrile
C12H11N3 *

E Param.: -13.30

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione
C18H15NO2 *

E Param.: -13.56

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-(p-methoxybenzylidene)-indan-1,3-dione
C17H12O3 *

E Param.: -11.32

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-benzylidene-indan-1,3-dione
C16H10O2 *

E Param.: -10.11

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
jul-indan-1,3-dione
C22H19NO2 *

E Param.: -14.68

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
aniBBS
C14H14N2O4 *

E Param.: -10.37

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dmaBBS
C15H17N3O3 *

E Param.: -12.76

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
julBBS
C19H21N3O3 *

E Param.: -13.84

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dma(S)BBS
C15H17N3O2S *

E Param.: -10.73

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
jul(S)BBS
C19H21N3O2S *

E Param.: -11.89

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
benzylidene-Meldrum's acid
C13H12O4 *

E Param.: -9.15

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(methoxy)benzylidene Meldrum's acid
C14H14O5 *

E Param.: -10.28

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(dimethylamino)benzylidene Meldrum's acid
C15H17NO4 *

E Param.: -12.76

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
jul Meldrum's acid
C19H21NO4 *

E Param.: -13.97

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
(E)-3-(4-nitro-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.33

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-3-(4-cyano-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.64

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-1,3-diphenylprop-2-en-1-one (in DMSO)
C15H12O *
 DMSO

E Param.: -19.39

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-4-(4-nitrophenyl)but-3-en-2-one (in DSMO)
C10H9NO3 *
 DMSO

E Param.: -19.36

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4-methyl-1-(4-nitrophenyl)pent-1-en-3-one (in DMSO)
C12H13NO3 *
 DMSO

E Param.: -19.17

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4,4-dimethyl-1-(4-nitrophenyl)pent-1-en-3-one
C13H15NO3 *
 DMSO

E Param.: -19.15

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
maleic anhydride
C4H4O3 *
 DMSO

E Param.: -11.31

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
N-methyl maleimide
C5H7NO2 *
 DMSO

E Param.: -14.07

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
fumaronitrile
C4H2N2 *
 DMSO

E Param.: -15.71

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
diethyl fumarate
C8H12O4 *
 DMSO

E Param.: -17.79

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
diethyl maleate
C8H12O4 *
 DMSO

E Param.: -19.49

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
ethenesulfonyl fluoride (ESF)
*
 DMSO

E Param.: -12.09

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
2-phenylethene-1-sulfonyl fluoride
C8H7FO2S *
 DMSO

E Param.: -16.63

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
(E)-4-phenylbut-3-en-2-one (in DMSO)
C10H10O *
 DMSO

E Param.: -23.01

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
cinnamonitrile (in DMSO)
C9H7N *
 DMSO

E Param.: -24.60

 * J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
methyl prop-2-enoate (in DMSO)
C4H6O2 *
 DMSO

E Param.: -18.84

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl prop-2-enoate (in DMSO)
C5H8O2 *
 DMSO

E Param.: -19.07

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
tert-butyl prop-2-enoate (in DMSO)
C7H12O2 *
 DMSO

E Param.: -20.22

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
N,N-dimethylprop-2-enamide (in DMSO)
C5H9NO *
 DMSO

E Param.: -23.54

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethenylsulfonylbenzene (in DMSO)
C8H8O2S *
 DMSO

E Param.: -18.36

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
acrylonitrile (in DMSO)
C3H3N *
 DMSO

E Param.: -19.05

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
but-3-en-2-one (in DMSO)
C4H6O *
 DMSO

E Param.: -16.76

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
1-phenylprop-2-en-1-one (in DMSO)
C9H8O *
 DMSO

E Param.: -15.25

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl 2-methylprop-2-enoate (in DMSO)
C6H10O2 *
 DMSO

E Param.: -22.77

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl (E)-but-2-enoate (in DMSO)
C6H10O2 *
 DMSO

E Param.: -23.59

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl cinnamate (in DMSO)
C11H12O2 *
 DMSO

E Param.: -24.52

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-1-methyl-4-(styrylsulfonyl)benzene (in DMSO)
C15H14O2S *
 DMSO

E Param.: -24.69

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
3-methylcyclopentenone
C6H8O *
 DMSO

E Param.: -28.90

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
2-methylcyclopentenone
C6H8O *
 DMSO

E Param.: -22.10

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclopentenone
C5H6O *
 DMSO

E Param.: -20.60

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
furan-2(5H)-one
C4H4O2 *
 DMSO

E Param.: -20.70

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
2-methylcyclohexenone
C7H10O *
 DMSO

E Param.: -27.50

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclohexenone
C6H8O *
 DMSO

E Param.: -22.10

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
dihydro-2H-pyran-2-one
C5H6O2 *
 DMSO

E Param.: -21.80

 ** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
3-methylenetetrahydropyran-2-one
C6H8O2 *
 DMSO

E Param.: -19.50

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
3-methylenedihydrofuranone
C5H6O2 *
 DMSO

E Param.: -19.40

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
3-methylcyclohexenone
C7H10O *
 DMSO

E Param.: -29.60

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
4-phenylbut-3-yn-2-one
C10H8O *

E Param.: -16.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
hex-3-yn-2-one
C6H8O *

E Param.: -17.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
cycloheptenone
C7H10O *
 DMSO

E Param.: -22.00

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
butynone
C4H4O *

E Param.: -16.60

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
(E)-2-(4-methoxybenzylidene)acenaphthylen-1(2H)-one
C20H14O2 *

E Param.: -18.72

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061