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

Tetrahedron

Cyclisatioh de diarylalcanes en milieu superacide: synthese de cetones tricycliques a methyle angulaire et mecanisme de leur isomerisation

C Berrier, JC Jacquesy, JP Gessom, A Renoux

Index: Berrier, C.; Jacquesy, J. C.; Gesson, J. P.; Renoux, A. Tetrahedron, 1984 , vol. 40, # 11 p. 1983 - 1994

Full Text: HTML

Citation Number: 4

Abstract

Cyclisation of readily available diary1-1, 2 ethanes 1→ 4 proceeds in SbF5,-HF at 0° C to yield tricyclic phenanthrenones 5, 6, 7 and 11 bearing an angular methyl group. This process implies the electrophilic attack of the more basic aromatic ring, reacting through its diprotonated form (on the oxygen and the meta carbon atom) on the second aromatic ring. Isomerization of these primary products may be observed to give ketones 8, 9, 10 from 3 ...

m-methoxybenzyl chloride Structure

m-methoxybenzyl...

~%

3-methoxybenzylmagnesium chloride Structure

3-methoxybenzyl...

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

~70%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

5-methoxy-2-methylbenzaldehyde Structure

5-methoxy-2-met...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

(5-Methoxy-2-methylphenyl)methanol Structure

(5-Methoxy-2-me...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

4a-Methyl-4,4a,9,10-tetrahydrophenanthrene-2(3H)-one Structure

4a-Methyl-4,4a,...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

methyl iodide Structure

~%

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

5-methoxy-2-methylbenzaldehyde Structure

5-methoxy-2-met...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(5-Methoxy-2-methylphenyl)methanol Structure

(5-Methoxy-2-me...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

2-methoxybenzylchloride Structure

2-methoxybenzyl...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

2-methoxybenzylmagnesium chloride Structure

2-methoxybenzyl...

~%

4-methoxy-2-[2-(2-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

5-methoxy-2-methylbenzaldehyde Structure

5-methoxy-2-met...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

Diethyl (4-methoxybenzyl)phosphonate Structure

Diethyl (4-meth...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(5-Methoxy-2-methylphenyl)methanol Structure

(5-Methoxy-2-me...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

4-Methoxybenzylchloride Structure

4-Methoxybenzyl...

~%

4-methoxy-2-[2-(4-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

5-methoxy-2-methylbenzaldehyde Structure

5-methoxy-2-met...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(5-Methoxy-2-methylphenyl)methanol Structure

(5-Methoxy-2-me...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

3-methoxybenzylmagnesium chloride Structure

3-methoxybenzyl...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

m-methoxybenzyl chloride Structure

m-methoxybenzyl...

~%

4-methoxy-2-[2-(3-methoxyphenyl)ethyl]-1-methylbenzene Structure

4-methoxy-2-[2-...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

5-methoxy-2-methylbenzaldehyde Structure

5-methoxy-2-met...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

(5-Methoxy-2-methylphenyl)methanol Structure

(5-Methoxy-2-me...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

Benzylmagnesium chloride Structure

Benzylmagnesium...

~%

4-methoxy-1-methyl-2-(2-phenylethyl)benzene Structure

4-methoxy-1-met...

Triethyl phosphate Structure

Triethyl phosphate

4-Methoxybenzylchloride Structure

4-Methoxybenzyl...

~92%

Diethyl (4-methoxybenzyl)phosphonate Structure

Diethyl (4-meth...

(4-methoxyphenyl)methyl-trimethyl-azanium Structure

(4-methoxypheny...

~%

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

Benzenemethanamine,4-methoxy-N,N-dimethyl- Structure

Benzenemethanam...

~%

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

1-(5-methoxy-2-methyl-phenyl)-N,N-dimethyl-methanamine Structure

1-(5-methoxy-2-...