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

Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides

…, PKG Hodgson, JJ Morrison, AO Oyewale

Index: Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 402 - 415

Full Text: HTML

Citation Number: 20

Abstract

Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4, 4′-bis (diphenylmethyl) ...

Neopentyl bromide Structure

Neopentyl bromide

~42%

2-Methylbut-2-ene Structure

2-Methylbut-2-ene

2-Methylbut-2-ene Structure

2-Methylbut-2-ene

Isobutylene Structure

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~%

4-Chlorotoluene Structure

4-Chlorotoluene

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

1-chloro-4-(2-phenylethyl)benzene Structure

1-chloro-4-(2-p...

Detail

Benzyl chloride Structure

Benzyl chloride

~0%

trans-Stilbene Structure

Diphenylmethane Structure

Diphenylmethane

Bibenzyl Structure

Detail

2,2-DICHLOROPROPANE Structure

2,2-DICHLOROPROPANE

~1%

2-chloropropene Structure

2-chloropropene

Allene Structure

2,3-dichloro-2,3-dimethylbutane Structure

2,3-dichloro-2,...

6-Chloro-1-hexyne Structure

6-Chloro-1-hexyne

~0%

METHYLENECYCLOPENTANE Structure

METHYLENECYCLOP...

Cyclopentane Structure

3-methylidenecyclopentene Structure

3-methylidenecy...

Detail

1,5-Dibromopentane Structure

1,5-Dibromopentane

~6%

trans-1,3-pentadiene Structure

trans-1,3-pentadiene

2-Pentene, (2E)- Structure

2-Pentene, (2E)-

Pent-1-ene Structure

Detail

4-Methoxybenzylchloride Structure

4-Methoxybenzyl...

~0%

4-Methylanisole Structure

4-Methylanisole

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

Benzene,1,1'-(1...

Benzene,1,1'-methylenebis[4-methoxy- Structure

Benzene,1,1'-me...

Detail

o-Xylylene dichloride Structure

o-Xylylene dich...

~0%

o-xylene Structure

Benzocyclobutene Structure

Benzocyclobutene

Dibenzo[a,e]cyclooctene,5,6,11,12-tetrahydro- Structure

Dibenzo[a,e]cyc...

Detail

1-Heptyne, 7-chloro- Structure

1-Heptyne, 7-chloro-

~%

3-methylidenecyclohexene Structure

3-methylidenecy...

4-methylidenecyclohexene Structure

4-methylidenecy...

Cyclohexane, methylene- Structure

Cyclohexane, me...

3-Fluoro-o-xylene Structure

3-Fluoro-o-xylene

~%

5-fluorobicyclo[4.2.0]octa-1(6),2,4-triene Structure

5-fluorobicyclo...

2,3-Dimethylaniline Structure

2,3-Dimethylaniline

~%

5-fluorobicyclo[4.2.0]octa-1(6),2,4-triene Structure

5-fluorobicyclo...

Triphenylmethyl Chloride Structure

Triphenylmethyl...

~47%

Triphenylmethane Structure

Triphenylmethane

1-benzhydryl-4-(4-benzhydrylphenyl)benzene Structure

1-benzhydryl-4-...

Bromodiphenylmethane Structure

Bromodiphenylmethane

~61%

Diphenylmethane Structure

Diphenylmethane

Benzene,1,1',1'',1'''-(1,2-ethanediylidene)tetrakis- Structure

Benzene,1,1',1'...

2,3-DIMETHYL-2-BUTANOL Structure

2,3-DIMETHYL-2-...

~49%

2-chloro-2,3-dimethylbutane Structure

2-chloro-2,3-di...

1-bromo-5-hexene Structure

1-bromo-5-hexene

~0%

1,3-hexadiene Structure

1,5-Hexadiene Structure

trans-1,4-Hexadiene Structure

trans-1,4-Hexadiene

Detail

1,2-Bis(bromomethyl)-3-fluorobenzene Structure

1,2-Bis(bromome...

~7%

3-Fluoro-o-xylene Structure

3-Fluoro-o-xylene

5-fluorobicyclo[4.2.0]octa-1(6),2,4-triene Structure

5-fluorobicyclo...

α-Bromo-o-xylene Structure

α-Bromo-o-xylene

~0%

o-xylene Structure

Benzocyclobutene Structure

Benzocyclobutene

Benzene,1,1'-(1,2-ethanediyl)bis[2-methyl- Structure

Benzene,1,1'-(1...

Detail

1,1-dichloropropane Structure

1,1-dichloropropane

~76%

N/A Structure

1,5-Hexadiene Structure

1-Propene, 1-chloro- Structure

1-Propene, 1-chloro-

Detail

1,2-dichlorocyclooctane Structure

1,2-dichlorocyc...

~27%

Cyclooctene Structure

1,3-cyclooctadiene Structure

1,3-cyclooctadiene

o-Chlorobenzylchloride Structure

o-Chlorobenzylc...

~%

2-Chlorotoluene Structure

2-Chlorotoluene

9,10-Dihydrophenanthrene Structure

9,10-Dihydrophe...

Benzene,1,1'-(1,2-ethanediyl)bis[2-chloro- Structure

Benzene,1,1'-(1...

Detail

2,3-Dimethylaniline Structure

2,3-Dimethylaniline

~%

1,2-Bis(bromomethyl)-3-fluorobenzene Structure

1,2-Bis(bromome...

Acetophenone Structure

~%

(E)-β-Chloroacrylophenone Structure

(E)-β-Chloroacr...

3-OXO-3-PHENYL-PROPIONALDEHYDE Structure

3-OXO-3-PHENYL-...

~%

(E)-β-Chloroacrylophenone Structure

(E)-β-Chloroacr...

2-Bromoacetophenone Structure

2-Bromoacetophenone

~%

(E)-β-Chloroacrylophenone Structure

(E)-β-Chloroacr...

6-Chloro-1-hexyne Structure

6-Chloro-1-hexyne

~22%

METHYLENECYCLOPENTANE Structure

METHYLENECYCLOP...

Cyclopentane Structure

3-methylidenecyclopentene Structure

3-methylidenecy...

Detail

4-Fluorobenzyl bromide Structure

4-Fluorobenzyl ...

~%

4-Fluorotoluene Structure

4-Fluorotoluene

1-(4-Fluorophenyl)-2-phenylethane Structure

1-(4-Fluorophen...

1-fluoro-4-[2-(4-fluorophenyl)ethyl]benzene Structure

1-fluoro-4-[2-(...

Detail

4-Fluorobenzyl chloride Structure

4-Fluorobenzyl ...

~%

4-Fluorotoluene Structure

4-Fluorotoluene

1-(4-Fluorophenyl)-2-phenylethane Structure

1-(4-Fluorophen...

N,N-Dimethylethanamine Structure

N,N-Dimethyleth...

Detail

Pinacol Structure

~64%

2,3-dichloro-2,3-dimethylbutane Structure

2,3-dichloro-2,...

2,2-DICHLOROPROPANE Structure

2,2-DICHLOROPROPANE

~6%

2-chloropropene Structure

2-chloropropene

Allene Structure

2,3-dichloro-2,3-dimethylbutane Structure

2,3-dichloro-2,...

1-chloro-4-phenylbutane Structure

1-chloro-4-phen...

~0%

1,2,3,4-Tetrahydronaphthalene Structure

1,2,3,4-Tetrahy...

Butylbenzene Structure

2,3-dichloro-2,3-dimethylbutane Structure

2,3-dichloro-2,...

~84%

2,3-DIMETHYL-1,3-BUTADIENE Structure

2,3-DIMETHYL-1,...

Pinacol Structure

~19%

Pinacolone Structure

tetramethylethylene Structure

tetramethylethylene

2,3-DIMETHYL-1,3-BUTADIENE Structure

2,3-DIMETHYL-1,...

Detail

1,3-Dichlorobutane Structure

1,3-Dichlorobutane

~38%

1-Butene Structure

2-butene Structure

butadiene Structure

4-Methoxybenzylchloride Structure

4-Methoxybenzyl...

~13%

4-Methylanisole Structure

4-Methylanisole

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

Benzene,1,1'-(1...

Benzene,1,1'-methylenebis[4-methoxy- Structure

Benzene,1,1'-me...

Detail

4-Bromobenzyl bromide Structure

4-Bromobenzyl b...

~%

2-Bromotoluene Structure

9,10-Dihydrophenanthrene Structure

9,10-Dihydrophe...

Benzene,1,1'-(1,2-ethanediyl)bis[2-bromo- Structure

Benzene,1,1'-(1...

Detail

α-Bromo-o-xylene Structure

α-Bromo-o-xylene

~70%

o-xylene Structure

Benzocyclobutene Structure

Benzocyclobutene

Benzene,1,1'-(1,2-ethanediyl)bis[2-methyl- Structure

Benzene,1,1'-(1...

Detail

4-Fluoro-o-xylene Structure

4-Fluoro-o-xylene

~78%

1,2-Bis(bromomethyl)-4-fluorobenzene Structure

1,2-Bis(bromome...

Butyraldehyde Structure

~31%

1,1-dichlorobutane Structure

1,1-dichlorobutane

4-Fluorobenzyl bromide Structure

4-Fluorobenzyl ...

~%

4-Fluorotoluene Structure

4-Fluorotoluene

1-(4-Fluorophenyl)-2-phenylethane Structure

1-(4-Fluorophen...

1-fluoro-4-[2-(4-fluorophenyl)ethyl]benzene Structure

1-fluoro-4-[2-(...

Detail

4-Fluorobenzyl chloride Structure

4-Fluorobenzyl ...

~%

4-Fluorotoluene Structure

4-Fluorotoluene

1-(4-Fluorophenyl)-2-phenylethane Structure

1-(4-Fluorophen...

N,N-Dimethylethanamine Structure

N,N-Dimethyleth...

Detail

1,6-Dibromohexane Structure

1,6-Dibromohexane

~0%

1-hexene Structure

cyclohexane Structure

1-Heptyne, 7-chloro- Structure

1-Heptyne, 7-chloro-

~%

3-methylidenecyclohexene Structure

3-methylidenecy...

4-methylidenecyclohexene Structure

4-methylidenecy...

Cyclohexane, methylene- Structure

Cyclohexane, me...

1-phenoxyethoxybenzene Structure

1-phenoxyethoxy...

~29%

phenyl vinyl ether Structure

phenyl vinyl ether

Benzaldehyde Structure

Toluene Structure

Detail

2,3,4,5,6-Pentafluorobenzylchloride Structure

2,3,4,5,6-Penta...

~33%

Benzene,1,2,3,4,5-pentafluoro-6-methyl- Structure

Benzene,1,2,3,4...

1,2,3,4,5-pentafluoro-6-[2-(2,3,4,5,6-pentafluorophenyl)ethyl]benzene Structure

1,2,3,4,5-penta...

(Pentafluorophenyl)methanol Structure

(Pentafluorophe...

~%

1,2,3,4,5-pentafluoro-6-[2-(2,3,4,5,6-pentafluorophenyl)ethyl]benzene Structure

1,2,3,4,5-penta...

1-Chloromethyl naphthalene Structure

1-Chloromethyl ...

~76%

1,2-Di(1-naphthyl)ethane Structure

1,2-Di(1-naphth...

1-Methylnaphthalene Structure

1-Methylnaphthalene

2-Phenyl-1-propanol Structure

2-Phenyl-1-propanol

~70%

1-BROMO-2-PHENYLPROPANE Structure

1-BROMO-2-PHENY...

4-Methylbenzyl chloride Structure

4-Methylbenzyl ...

~0%

(E)-1,2-Bis(4-methylphenyl)ethene Structure

(E)-1,2-Bis(4-m...

p-Xylene Structure

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

Detail

1,4-Dibromopentane Structure

1,4-Dibromopentane

~46%

trans-1,3-pentadiene Structure

trans-1,3-pentadiene

1,4-Pentadiene Structure

2-Pentene, (2E)- Structure

2-Pentene, (2E)-

Detail

1,5-Dibromopentane Structure

1,5-Dibromopentane

~17%

trans-1,3-pentadiene Structure

trans-1,3-pentadiene

2-Pentene, (2E)- Structure

2-Pentene, (2E)-

Pent-1-ene Structure

Detail

2-Bromoacetophenone Structure

2-Bromoacetophenone

~%

3-OXO-3-PHENYL-PROPIONALDEHYDE Structure

3-OXO-3-PHENYL-...

1,1-dichloropropane Structure

1,1-dichloropropane

~0%

N/A Structure

1,5-Hexadiene Structure

1-Propene, 1-chloro- Structure

1-Propene, 1-chloro-

Detail

α-Bromo-o-xylene Structure

α-Bromo-o-xylene

~0%

o-xylene Structure

Benzocyclobutene Structure

Benzocyclobutene

Benzene,1,1'-(1,2-ethanediyl)bis[2-methyl- Structure

Benzene,1,1'-(1...

Detail

1,1-dichloropropane Structure

1,1-dichloropropane

~0%

N/A Structure

1,5-Hexadiene Structure

1-Propene, 1-chloro- Structure

1-Propene, 1-chloro-

Detail

1-bromo-5-hexene Structure

1-bromo-5-hexene

~0%

1,3-hexadiene Structure

1,5-Hexadiene Structure

trans-1,4-Hexadiene Structure

trans-1,4-Hexadiene

Detail

2-Fluorobenzyl bromide Structure

2-Fluorobenzyl ...

~%

2-Fluorotoluene Structure

2-Fluorotoluene

Phenanthrene Structure

9,10-Dihydrophenanthrene Structure

9,10-Dihydrophe...

Detail

2-Fluorobenzyl chloride Structure

2-Fluorobenzyl ...

~%

Phenanthrene Structure

9,10-Dihydrophenanthrene Structure

9,10-Dihydrophe...

1,2-Bis(2-fluorophenyl)ethane Structure

1,2-Bis(2-fluor...

Detail

1-chloro-4-phenylbutane Structure

1-chloro-4-phen...

~35%

1,2,3,4-Tetrahydronaphthalene Structure

1,2,3,4-Tetrahy...

Butylbenzene Structure

3,4-Dimethylaniline Structure

3,4-Dimethylaniline

~57%

4-Fluoro-o-xylene Structure

4-Fluoro-o-xylene

1,2-Bis(bromomethyl)-4-fluorobenzene Structure

1,2-Bis(bromome...

~7%

4-Fluoro-o-xylene Structure

4-Fluoro-o-xylene

4-fluorobenzocyclobutene Structure

4-fluorobenzocy...

4-Chlorobenzyl chloride Structure

4-Chlorobenzyl ...

~%

4-Chlorotoluene Structure

4-Chlorotoluene

Bis(p-chlorophenyl)ethane Structure

Bis(p-chlorophe...

1-chloro-4-(2-phenylethyl)benzene Structure

1-chloro-4-(2-p...

Detail

1,3-Dichlorobutane Structure

1,3-Dichlorobutane

~0%

1-Butene Structure

2-butene Structure

butadiene Structure

(Pentafluorophenyl)methanol Structure

(Pentafluorophe...

~80%

2,3,4,5,6-Pentafluorobenzylchloride Structure

2,3,4,5,6-Penta...

4-Methylbenzyl chloride Structure

4-Methylbenzyl ...

~60%

(E)-1,2-Bis(4-methylphenyl)ethene Structure

(E)-1,2-Bis(4-m...

p-Xylene Structure

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

Detail

1,6-Dibromohexane Structure

1,6-Dibromohexane

~73%

1-hexene Structure

cyclohexane Structure

4-Methylbenzyl chloride Structure

4-Methylbenzyl ...

~0%

(E)-1,2-Bis(4-methylphenyl)ethene Structure

(E)-1,2-Bis(4-m...

p-Xylene Structure

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

Detail

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