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

The Journal of Organic Chemistry

Cyclizations of. omega.-allenyl radicals

M Apparu, JK Crandall

Index: Apparu, Marcel; Crandall, Jack K. Journal of Organic Chemistry, 1984 , vol. 49, # 12 p. 2125 - 2130

Full Text: HTML

Citation Number: 44

Abstract

Allenyl halides of structure (CH3) 2C= C= CH (CH2), X with n= 3-6 have been prepared and reacted with n-Bu3SnH to generate the corresponding radicals for examination of the cyclization reactions of these reactive intermediates. The observed hydrocarbon products indicate that cyclization occurs for the n= 3, 4, and 5 radicals but not for the n= 6 species. The n= 3 radical isomerizes very efficiently by intramolecular addition to the sp carbon of ...

1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI) Structure

1,2-Butadiene,3...

~%

Isopropylidenecyclohexane Structure

Isopropylidenec...

1-bromo-3-methylbuta-1,2-diene Structure

1-bromo-3-methy...

~%

Isopropylidenecyclohexane Structure

Isopropylidenec...

Bromo(isopropyl)magnesium Structure

Bromo(isopropyl...

Cyclohexanone Structure

~%

Isopropylidenecyclohexane Structure

Isopropylidenec...

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

N/A Structure

~%

6-methyl-hepta-4,5-dienylamine Structure

6-methyl-hepta-...

Isopropylidenecyclohexane Structure

Isopropylidenec...

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

Detail

1-bromo-3-methylbuta-1,2-diene Structure

1-bromo-3-methy...

~72%

1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI) Structure

1,2-Butadiene,3...

METHYLLITHIUM Structure

2-(1-Propynyl)tetrahydrofuran Structure

2-(1-Propynyl)t...

~94%

6-methylhepta-4,5-dien-1-ol Structure

6-methylhepta-4...

N/A Structure

~74%

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

6-methylhepta-4,5-dien-1-ol Structure

6-methylhepta-4...

~%

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

2-(1-Propynyl)tetrahydrofuran Structure

2-(1-Propynyl)t...

~%

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

1-(2-tetrahydropyranyloxy)-6-methyl-hepta-4,5-diene Structure

1-(2-tetrahydro...

~%

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI) Structure

1,2-Butadiene,3...

~%

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

1-bromo-3-methylbuta-1,2-diene Structure

1-bromo-3-methy...

~%

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

Bromo(isopropyl)magnesium Structure

Bromo(isopropyl...

Cyclohexanone Structure

~%

Isopropylidenecyclohexane Structure

Isopropylidenec...

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

N/A Structure

~%

6-methyl-hepta-4,5-dienylamine Structure

6-methyl-hepta-...

Isopropylidenecyclohexane Structure

Isopropylidenec...

1-propan-2-ylcyclohexene Structure

1-propan-2-ylcy...

Detail

Bromo(isopropyl)magnesium Structure

Bromo(isopropyl...

Cycloheptanone Structure

~%

ISO-PROPYLIDENECYCLOHEPTANE Structure

ISO-PROPYLIDENE...

1-Isopropylcycloheptene Structure

1-Isopropylcycl...

6-methylhepta-4,5-dien-1-ol Structure

6-methylhepta-4...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

2-(1-Propynyl)tetrahydrofuran Structure

2-(1-Propynyl)t...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-(2-tetrahydropyranyloxy)-6-methyl-hepta-4,5-diene Structure

1-(2-tetrahydro...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

N/A Structure

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

2-methylhepta-2,3-diene Structure

2-methylhepta-2...

Bromo(isopropyl)magnesium Structure

Bromo(isopropyl...

Cyclopentanone Structure

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI) Structure

1,2-Butadiene,3...

~%

2-methylprop-1-enylcyclohexane Structure

2-methylprop-1-...

1-bromo-3-methylbuta-1,2-diene Structure

1-bromo-3-methy...

~%

2-methylprop-1-enylcyclohexane Structure

2-methylprop-1-...

1-Iodo-8-methyl-6,7-nonadiene Structure

1-Iodo-8-methyl...

~%

2-Methyl-2,3-nonadiene Structure

2-Methyl-2,3-no...

2-methylprop-1-enylcyclohexane Structure

2-methylprop-1-...

trans-2-methyl-2,4-nonadiene Structure

trans-2-methyl-...

1,6-diiodohexane Structure

1,6-diiodohexane

~%

2-methyldeca-1,3-diene Structure

2-methyldeca-1,...

1,2-Butadiene,3-methyl- (6CI,7CI,8CI,9CI) Structure

1,2-Butadiene,3...

~%

2-methyldeca-1,3-diene Structure

2-methyldeca-1,...

1-bromo-3-methylbuta-1,2-diene Structure

1-bromo-3-methy...

~%

2-methyldeca-1,3-diene Structure

2-methyldeca-1,...

N/A Structure

~%

2-methyldeca-1,3-diene Structure

2-methyldeca-1,...

N/A Structure

2-Methyl-2,4-decadiene Structure

2-Methyl-2,4-de...

6-methylhepta-4,5-dien-1-ol Structure

6-methylhepta-4...

~%

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

2-(1-Propynyl)tetrahydrofuran Structure

2-(1-Propynyl)t...

~%

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

1-(2-tetrahydropyranyloxy)-6-methyl-hepta-4,5-diene Structure

1-(2-tetrahydro...

~%

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

N/A Structure

~%

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

2-methylhepta-2,3-diene Structure

2-methylhepta-2...

Bromo(isopropyl)magnesium Structure

Bromo(isopropyl...

Cyclopentanone Structure

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

7-bromo-2-methylhepta-2,3-diene Structure

7-bromo-2-methy...

~%

Isopropylidenecyclopentane Structure

Isopropylidenec...

1-ISO-PROPYLCYCLOPENTENE Structure

1-ISO-PROPYLCYC...

BF 3· OEt 2 promotes fast, mild, clean and regioselective de...

[Posner; Shulman-Roskes; Oh; Carry; Green; Clark; Dai; Anjeh Tetrahedron Letters, 1991 , vol. 32, # 45 p. 6489 - 6492]

New synthesis of olefins

[Kornblum,N. et al. Journal of the American Chemical Society, 1971 , vol. 93, p. 4316 - 4318]

Dehydration of Alcohols, Diols, and Related Compounds in Dim...

[Traynelis,V.J. et al. Journal of Organic Chemistry, 1964 , vol. 29, p. 123 - 129]

Dehydration of Alcohols, Diols, and Related Compounds in Dim...

[Traynelis,V.J. et al. Journal of Organic Chemistry, 1964 , vol. 29, p. 123 - 129]

Investigations on selective bromination of tertiary hydrogen...

[Siegmann,R.H. et al. Recueil des Travaux Chimiques des Pays-Bas, 1964 , vol. 83, p. 67 - 80]