Mayr's Database of Reactivity Parameters

Ylides

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
Ph3P=CH-CO2Et
*
dichloromethane

N  Param.: 12.79

sN Param.: 0.77
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 12.21

sN Param.: 0.62
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=C(CH3)-CO2Et
*
dichloromethane

N  Param.: 13.09

sN Param.: 0.73
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CN
*
dichloromethane

N  Param.: 12.29

sN Param.: 0.75
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-COPh
*
dichloromethane

N  Param.: 9.54

sN Param.: 0.97
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(4-Br-C6H4)-(CO)-CH=SMe2
*
dichloromethane

N  Param.: 11.95

sN Param.: 0.76
***Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
Me2S=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 15.85

sN Param.: 0.61
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
Me2S=CH-CN (in DMSO)
*
DMSO

N  Param.: 16.23

sN Param.: 0.60
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 13.78

sN Param.: 0.72
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(C6H5)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 13.95

sN Param.: 0.69
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 14.48

sN Param.: 0.71
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 15.68

sN Param.: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S=CH(p-NO2-C6H4) (in DMSO)
*
DMSO

N  Param.: 18.42

sN Param.: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S=CH(4-CN-C6H4) (in DMSO)
*
DMSO

N  Param.: 21.07

sN Param.: 0.68
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S(O)=CH2 (in DMSO)
*
DMSO

N  Param.: 21.29

sN Param.: 0.47
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C9H12NO2*
DMSO

N  Param.: 26.71

sN Param.: 0.37
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C11H17N2O*
DMSO

N  Param.: 27.45

sN Param.: 0.38
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)
C7H7N2*
DMSO

N  Param.: 25.94

sN Param.: 0.42
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)
C8H10NO*
DMSO

N  Param.: 20.24

sN Param.: 0.60
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C13H12NO*
DMSO

N  Param.: 19.46

sN Param.: 0.58
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C15H17N2O*
DMSO

N  Param.: 21.61

sN Param.: 0.58
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C13H11ClNO*
DMSO

N  Param.: 17.98

sN Param.: 0.63
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)
C17H14NO*
DMSO

N  Param.: 19.38

sN Param.: 0.50
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C17H14NO*
DMSO

N  Param.: 20.08

sN Param.: 0.57
***J. Am. Chem. Soc. 2013, 135, 15216–15224
10.1021/ja407885h
Meldrum's acid iodonium ylide (in CH2Cl2)
*
dichloromethane

N  Param.: 4.36

sN Param.: 1.06
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
Dimedone iodonium ylide (in CH2Cl2)
*
dichloromethane

N  Param.: 6.18

sN Param.: 0.81
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)
*
dichloromethane

N  Param.: 7.98

sN Param.: 0.71
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)
*
dichloromethane

N  Param.: 4.67

sN Param.: 0.92
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768