Mayr's Database of Reactivity Parameters

Enol Ethers

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles » Enol Ethers

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
Danishefskys diene
C8H16O2Si *
 dichloromethane

N  Param.: 8.57

sN Param.: 0.84		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran
C8H16O2Si *
 dichloromethane

N  Param.: 10.61

sN Param.: 0.86		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
5-(trimethylsiloxy)-2,3-dihydrofuran
C7H14O2Si *
 dichloromethane

N  Param.: 12.56

sN Param.: 0.70		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(trimethylsiloxy)cyclohexene
C9H18OSi *
 dichloromethane

N  Param.: 5.21

sN Param.: 1.00		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(trimethylsiloxy)propene
C6H14OSi *
 dichloromethane

N  Param.: 5.41

sN Param.: 0.91		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-phenyl-1-(trimethylsiloxy)ethene
C11H16OSi *
 dichloromethane

N  Param.: 6.22

sN Param.: 0.96		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(trimethylsiloxy)cyclopentene
C8H16OSi *
 dichloromethane

N  Param.: 6.57

sN Param.: 0.93		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-phenoxy-1-(trimethylsiloxy)ethene
C11H16O2Si *
 dichloromethane

N  Param.: 8.23

sN Param.: 0.81		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(triisopropylsiloxy)ethene
C11H24OSi *
 dichloromethane

N  Param.: 3.44

sN Param.: 0.94		 ** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(triisopropylsiloxy)propene
C12H26OSi *
 dichloromethane

N  Param.: 5.38

sN Param.: 0.85		 ** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
3,3-dimethyl-2-(trimethylsiloxy)buten
C9H20OSi *
 dichloromethane

N  Param.: 3.78

sN Param.: 0.79		 ** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-methoxy-2-methyl-1-(trimethylsiloxy)propene
C8H18O2Si *
 dichloromethane

N  Param.: 9.00

sN Param.: 0.98		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methyl-1-(trimethylsiloxy)propen
C7H16OSi *
 dichloromethane

N  Param.: 3.94

sN Param.: 1.00		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(Z)-1-(triisopropylsiloxy)propen
C12H26OSi *
 dichloromethane

N  Param.: 3.87

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,2-bis(trimethylsiloxy)cyclohexene
C12H26O2Si2 *
 dichloromethane

N  Param.: 4.46

sN Param.: 1.15		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(trimethylsiloxy)buta-1,3-diene
C7H14OSi *
 dichloromethane

N  Param.: 4.83

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)buta-1,3-diene
C7H14OSi *
 dichloromethane

N  Param.: 4.60

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)cycloheptene
C10H20OSi *
 dichloromethane

N  Param.: 6.62

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)cyclooctene
C11H22OSi *
 dichloromethane

N  Param.: 6.77

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
Z-3-(trimethylsiloxy)pent-2-ene
C8H18OSi *
 dichloromethane

N  Param.: 5.58

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(trimethylsiloxy)furan
C7H12O2Si *
 dichloromethane

N  Param.: 7.22

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
ethyl-vinylether
C4H8O *
 dichloromethane

N  Param.: 3.92

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
isobutylenyl-ethylether
C6H12O *
 dichloromethane

N  Param.: 4.23

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1-diethoxyethene
C6H12O2 *
 dichloromethane

N  Param.: 9.81

sN Param.: 0.81		 *** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1-butoxy-1-(trimethylsiloxy)ethene
C9H20O2Si *
 dichloromethane

N  Param.: 10.21

sN Param.: 0.82		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene
C12H26O2Si *
 dichloromethane

N  Param.: 10.32

sN Param.: 0.79		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1,1-bis(trimethylsiloxy)propene
C9H22O2Si2 *
 dichloromethane

N  Param.: 10.38

sN Param.: 0.87		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran
C8H16O2Si *
 dichloromethane

N  Param.: 11.50

sN Param.: 0.91		 *** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran
C22H5F15O2Si *
 dichloromethane

N  Param.: 8.16

sN Param.: 0.67		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
5-(triphenylsiloxy)-2,3-dihydrofuran
C22H20O2Si *
 dichloromethane

N  Param.: 11.28

sN Param.: 0.91		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(triphenylsiloxy)cyclopentene
C23H22OSi *
 dichloromethane

N  Param.: 5.76

sN Param.: 1.02		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2,3-dihydrofuran
C4H6O *
 dichloromethane

N  Param.: 4.37

sN Param.: 0.90		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2-(tris(pentafluorophenyl)siloxy)-propene
C21H5F15OSi *
 dichloromethane

N  Param.: 0.58

sN Param.: 0.91		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(tris(pentafluorophenyl)siloxy)-cyclopentene
C23H7F15OSi *
 dichloromethane

N  Param.: 1.38

sN Param.: 0.93		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2-(tris(trimethylsilyl)siloxy)propene
*
 dichloromethane

N  Param.: 6.04

sN Param.: 0.82		 *** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
1-(tris(trimethylsilyl)siloxy)cyclohexene
*
 dichloromethane

N  Param.: 5.07

sN Param.: 0.91		 *** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
(tris(trimethylsilyl)siloxy)ethene
*
 dichloromethane

N  Param.: 4.01

sN Param.: 0.83		 *** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)
*
 MeCN

N  Param.: 12.34

sN Param.: 0.72		 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)
*
 MeCN

N  Param.: 10.52

sN Param.: 0.78		 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)
*
 MeCN

N  Param.: 9.11

sN Param.: 0.88		 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene
*
 dichloromethane

N  Param.: 1.47

sN Param.: 0.89		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
3,3,3-trifluoro-2-(trimethylsiloxy)propene
*
 dichloromethane

N  Param.: -2.94

sN Param.: 1.11		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene
*
 dichloromethane

N  Param.: -3.52

sN Param.: 1.17		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
2-(triphenylsiloxy)propene
*
 dichloromethane

N  Param.: 4.46

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3-methyl-2-(trimethylsiloxy)but-1-ene
*
 dichloromethane

N  Param.: 5.41

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene
*
 dichloromethane

N  Param.: 5.58

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
n-butyl vinyl ether
*
 dichloromethane

N  Param.: 3.76

sN Param.: 0.91		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
1-(trimethylsiloxy)cyclopentene (in MeCN)
C8H16OSi *
 MeCN

N  Param.: 6.43

sN Param.: 0.89		 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)
C17H20OSi *
 MeCN

N  Param.: 3.00

sN Param.: 0.83		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)
C12H18OSi *
 MeCN

N  Param.: 5.18

sN Param.: 0.94		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634