e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Activation of Electrophilicity of Stable Y-Delocalized Carbamate Cations in Intramolecular Aromatic Substitution Reaction: Evidence for Formation of Diprotonated …

…, K Kawamoto, H Sugimoto, S Nakamura…

Index: Kurouchi, Hiroaki; Kawamoto, Kyoko; Sugimoto, Hiromichi; Nakamura, Satoshi; Otani, Yuko; Ohwada, Tomohiko Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 9313 - 9328,16

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Citation Number: 10

Abstract

Although cations with three heteroatoms, such as monoprotonated guanidine and urea, are stabilized by Y-shaped conjugation and such Y-conjugated cations are sufficiently basic to be further protonated (or protosolvated) to dications in strongly acid media, only O- monoprotonated species have been detected in the case of carbamates even in magic acid. We found that the trifluoromethanesulfonic acid-catalyzed cyclization of ...

2-4-chlorophenylethylcarbamic acid methyl ester Structure

2-4-chloropheny...

~93%

7-Chloro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Chloro-3,4-di...

2-4-chlorophenylethylcarbamic acid methyl ester Structure

2-4-chloropheny...

~86%

7-Chloro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Chloro-3,4-di...

4-chlorobenzeneethanamine Structure

4-chlorobenzene...

4-chlorobenzeneethanamine Structure

4-chlorobenzene...

~%

7-Chloro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Chloro-3,4-di...

N/A Structure

~42%

5,7-dichloro-3,4-dihydro-2H-isoquinolin-1-one Structure

5,7-dichloro-3,...

2-(2,4-Dichlorophenyl)ethanamine Structure

2-(2,4-Dichloro...

methyl N-(3-phenylpropyl)carbamate Structure

methyl N-(3-phe...

~79%

2,3,4,5-Tetrahydro-1H-2-benzazepin-1-one Structure

2,3,4,5-Tetrahy...

Carbamic acid, (2-phenylethyl)-, Methyl ester Structure

Carbamic acid, ...

methyl iodide Structure

~84%

methyl N-methyl-N-(2-phenylethyl)carbamate Structure

methyl N-methyl...

2-Phenylethanamine Structure

2-Phenylethanamine

~%

methyl N-methyl-N-(2-phenylethyl)carbamate Structure

methyl N-methyl...

2-Phenylethanamine Structure

2-Phenylethanamine

Methyl chloroformate Structure

Methyl chloroformate

~97%

Carbamic acid, (2-phenylethyl)-, Methyl ester Structure

Carbamic acid, ...

2-4-fluorophenylethylcarbamic acid methyl ester Structure

2-4-fluoropheny...

~93%

7-Fluoro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Fluoro-3,4-di...

4-Fluorophenethylamine Structure

4-Fluoropheneth...

~%

7-Fluoro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Fluoro-3,4-di...

2-4-fluorophenylethylcarbamic acid methyl ester Structure

2-4-fluoropheny...

~%

7-Fluoro-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Fluoro-3,4-di...

4-Fluorophenethylamine Structure

4-Fluoropheneth...

(2-phenyl-propyl)carbamic acid methyl ester Structure

(2-phenyl-propy...

~85%

4-Methyl-3,4-dihydro-1(2H)-isoquinolinone Structure

4-Methyl-3,4-di...

methyl N-[2-(4-methoxyphenyl)ethyl]carbamate Structure

methyl N-[2-(4-...

~95%

methyl N-[2-(4-hydroxyphenyl)ethyl]carbamate Structure

methyl N-[2-(4-...

4-Methoxyphenylethylamine Structure

4-Methoxyphenyl...

~%

methyl N-[2-(4-hydroxyphenyl)ethyl]carbamate Structure

methyl N-[2-(4-...

N/A Structure

~40%

5,7-dichloro-3,4-dihydro-2H-isoquinolin-1-one Structure

5,7-dichloro-3,...

2-(2,4-Dichlorophenyl)ethanamine Structure

2-(2,4-Dichloro...

2-(2,4-Dichlorophenyl)ethanamine Structure

2-(2,4-Dichloro...

~%

5,7-dichloro-3,4-dihydro-2H-isoquinolin-1-one Structure

5,7-dichloro-3,...

methyl N-[2-(4-methoxyphenyl)ethyl]carbamate Structure

methyl N-[2-(4-...

~79%

7-Hydroxy-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Hydroxy-3,4-d...

methyl N-[2-(4-hydroxyphenyl)ethyl]carbamate Structure

methyl N-[2-(4-...

~83%

7-Hydroxy-3,4-dihydro-1(2H)-isoquinolinone Structure

7-Hydroxy-3,4-d...

Phenethyl isocyanate Structure

Phenethyl isocyanate

~78%

3,4-Dihydroisoquinolin-1(2H)-one Structure

3,4-Dihydroisoq...