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

Canadian Journal of Chemistry

The sec-butyl cation; reaction with 2-butene

P Lachance, AM Eastham

Index: Lachance, Pierre; Eastham, Arthur M. Canadian Journal of Chemistry, 1981 , vol. 59, p. 2621 - 2628

Full Text: HTML

Citation Number: 4

Abstract

The products from the reaction of 2-butene with BF3. CH3OH are olefins in the range C8 to above C20; about 60% of the product is the normal dimer-trimer-tetramer material but the remaining 40% is rearranged product. We have identified most of the skeletal structures up to C13 and suggest that the rearrangements are most easily interpreted by postulating that akyl transfers can occur in the same way as proton transfers.

3-Penten-2-one Structure

~%

3,3,4,6-tetramethyloctane Structure

3,3,4,6-tetrame...

1,1-DIMETHYLPROPYLMAGNESIUM CHLORIDE Structure

1,1-DIMETHYLPRO...

~%

3,3,4,6-tetramethyloctane Structure

3,3,4,6-tetrame...

ETHYLMAGNESIUM BROMIDE Structure

ETHYLMAGNESIUM ...

4,5,5-trimethyl-2-heptanone Structure

4,5,5-trimethyl...

~%

3,3,4,6-tetramethyloctane Structure

3,3,4,6-tetrame...

sec-Butyllithium solution Structure

sec-Butyllithiu...

4-Methyl-2-pentanone Structure

4-Methyl-2-pentanone

~29%

2,4,5-trimethylheptan-4-ol Structure

2,4,5-trimethyl...

Mesityl oxide Structure

~%

3,3,5-trimethylheptane Structure

3,3,5-trimethyl...

4,4-Dimethylhexan-2-one Structure

4,4-Dimethylhex...

ETHYLMAGNESIUM BROMIDE Structure

ETHYLMAGNESIUM ...

~%

3,3,5-trimethylheptane Structure

3,3,5-trimethyl...

3-methyl-3-penten-2-ol Structure

3-methyl-3-pent...

TERT-BUTYLMAGNESIUM CHLORIDE Structure

TERT-BUTYLMAGNE...

~63%

3,4,5,5-tetramethylhexan-2-one Structure

3,4,5,5-tetrame...

tetramethylethylene Structure

tetramethylethylene

~%

2,3,3,4-tetramethylhexane Structure

2,3,3,4-tetrame...

4,4,5-trimethyl-hexan-3-one Structure

4,4,5-trimethyl...

METHYLLITHIUM Structure

~%

2,3,3,4-tetramethylhexane Structure

2,3,3,4-tetrame...

METHYLLITHIUM Structure

methyl 2,2,3-trimethylpentanoate Structure

methyl 2,2,3-tr...

~%

2,3,3,4-tetramethylhexane Structure

2,3,3,4-tetrame...

3,4-Dimethyl-3-penten-2-one Structure

3,4-Dimethyl-3-...

~%

2,3,4,4-tetramethylhexane Structure

2,3,4,4-tetrame...

METHYLLITHIUM Structure

3,4,4-trimethyl-2-hexanone Structure

3,4,4-trimethyl...

~%

2,3,4,4-tetramethylhexane Structure

2,3,4,4-tetrame...

sec-Butyllithium solution Structure

sec-Butyllithiu...

5-Methyl-3-heptanon Structure

5-Methyl-3-heptanon

~%

4-ethyl-3,6-dimethyloctane Structure

4-ethyl-3,6-dim...

1,1-DIMETHYLPROPYLMAGNESIUM CHLORIDE Structure

1,1-DIMETHYLPRO...

~%

2,3,4,5,5-pentamethylheptane Structure

2,3,4,5,5-penta...

METHYLLITHIUM Structure

3,4,5,5-tetramethyl-2-heptanone Structure

3,4,5,5-tetrame...

~%

2,3,4,5,5-pentamethylheptane Structure

2,3,4,5,5-penta...

3-methyl-3-penten-2-ol Structure

3-methyl-3-pent...

~%

2,3,4,5,5-pentamethylheptane Structure

2,3,4,5,5-penta...

2,4,5-trimethylheptan-4-ol Structure

2,4,5-trimethyl...

~%

2,4,5-trimethylheptane Structure

2,4,5-trimethyl...

3,4-dimethylpentan-2-one Structure

3,4-dimethylpen...

magnesium,2-methanidylbutane,bromide Structure

magnesium,2-met...

~%

2,3,4,6-tetramethyloctane Structure

2,3,4,6-tetrame...

3,3-dimethylpentan-2-one Structure

3,3-dimethylpen...

magnesium,2-methylbutane,chloride Structure

magnesium,2-met...

~%

2,5,6,6-tetramethyloctane Structure

2,5,6,6-tetrame...

3-methyl-3-penten-2-ol Structure

3-methyl-3-pent...

~%

2,2,3,4-tetramethylhexane Structure

2,2,3,4-tetrame...

3,4,5,5-tetramethylhexan-2-one Structure

3,4,5,5-tetrame...

~%

2,2,3,4-tetramethylhexane Structure

2,2,3,4-tetrame...

Pinacolone Structure

sec-Butyllithium solution Structure

sec-Butyllithiu...

~%

2,2,3,4-tetramethylhexane Structure

2,2,3,4-tetrame...