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

Tetrahedron letters

Metal-halogen exchange-initiated cyclization of iodo carbonyl compounds

MP Cooke, IN Houpis

Index: Cooke, Manning P.; Houpis, Ioannis N. Tetrahedron Letters, 1985 , vol. 26, # 41 p. 4987 - 4990

Full Text: HTML

Citation Number: 47

Abstract

Abstract The feasibility of constructing carbocycles through the metal-halogen exchange- initiated cyclization reactions of iodoketones and other carboxyl derivatives has been studied. With saturated primary iodides, cyclization predominates when deactivated ketones are employed.

Tert-Butyllithium Structure

Tert-Butyllithium

~79%

3-isopropyl-2,2-dimethyl-heptan-3-ol Structure

3-isopropyl-2,2...

3-Heptanone, 2-methyl- Structure

3-Heptanone, 2-...

1-propan-2-ylcyclopentan-1-ol Structure

1-propan-2-ylcy...

5-Chloropentanal Structure

5-Chloropentanal

~%

1-propan-2-ylcyclopentan-1-ol Structure

1-propan-2-ylcy...

7-Chloro-2-methyl-3-heptanone Structure

7-Chloro-2-meth...

~%

1-propan-2-ylcyclopentan-1-ol Structure

1-propan-2-ylcy...

N,N-diethyl-6-iodohexanamide Structure

N,N-diethyl-6-i...

~5%

Caproic acid diethylamide Structure

Caproic acid di...

Cyclohexanone Structure

5-Chloropentanal Structure

5-Chloropentanal

~%

6-chlorohexan-2-ol Structure

6-chlorohexan-2-ol

ethyl 5-iodopentanoate Structure

ethyl 5-iodopen...

~%

Cyclopentanol, 1-butyl- Structure

Cyclopentanol, ...

Cyclopentanone Structure

5,5-dimethoxy-1-iodo-1(Z)-pentene Structure

5,5-dimethoxy-1...

~%

2,2-dimethylhept-6-en-3-ol Structure

2,2-dimethylhep...

Tert-Butyllithium Structure

Tert-Butyllithium

(Z)-5-iodo-4-pentenal Structure

(Z)-5-iodo-4-pe...

~20%

2-Cyclopentenol Structure

2-Cyclopentenol

2,2-dimethylhept-6-en-3-ol Structure

2,2-dimethylhep...

8-iodooctan-4-one Structure

8-iodooctan-4-one

~50%

4-Octanone Structure

Cyclopentanol,1-propyl- Structure

Cyclopentanol,1...

N/A Structure

5-Chloropentanal Structure

5-Chloropentanal

~%

Cyclopentanol,1-propyl- Structure

Cyclopentanol,1...

8-chlorooctan-4-ol Structure

8-chlorooctan-4-ol

~%

Cyclopentanol,1-propyl- Structure

Cyclopentanol,1...

8-chlorooctan-4-one Structure

8-chlorooctan-4-one

~%

Cyclopentanol,1-propyl- Structure

Cyclopentanol,1...

Tert-Butyllithium Structure

Tert-Butyllithium

8-iodooctan-4-one Structure

8-iodooctan-4-one

~49%

4-Octanone Structure

Cyclopentanol,1-propyl- Structure

Cyclopentanol,1...

Detail

8-chlorooctan-4-ol Structure

8-chlorooctan-4-ol

~%

8-chlorooctan-4-one Structure

8-chlorooctan-4-one

N/A Structure

~86%

methyl-butyl-γ-butenyl-carbinol Structure

methyl-butyl-γ-...

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

6-iodo-5(Z)-hexen-2-ol Structure

6-iodo-5(Z)-hex...

~%

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

5,5-dimethoxy-1-iodo-1(Z)-pentene Structure

5,5-dimethoxy-1...

~%

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

(Z)-5-iodo-4-pentenal Structure

(Z)-5-iodo-4-pe...

~%

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

n-Butyllithium Structure

N/A Structure

~86%

methyl-butyl-γ-butenyl-carbinol Structure

methyl-butyl-γ-...

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

Tert-Butyllithium Structure

Tert-Butyllithium

N/A Structure

~19%

2,2,3-trimethyl-6-hepten-3-ol Structure

2,2,3-trimethyl...

1-methylcyclopent-2-en-1-ol Structure

1-methylcyclope...

5-Chloropentanal Structure

5-Chloropentanal

~%

8-chlorooctan-4-one Structure

8-chlorooctan-4-one

5-Chloropentanal Structure

5-Chloropentanal

~%

Cyclopentanol,1-phenyl- Structure

Cyclopentanol,1...

5-chloro-1-phenylpentan-1-one Structure

5-chloro-1-phen...

~%

Cyclopentanol,1-phenyl- Structure

Cyclopentanol,1...

1-phenyl-5-chloropentan-1-ol Structure

1-phenyl-5-chlo...

~%

Cyclopentanol,1-phenyl- Structure

Cyclopentanol,1...

1-iodo-5-hexanone Structure

1-iodo-5-hexanone

~20%

2,2,3-trimethylheptan-3-ol Structure

2,2,3-trimethyl...

2-Hexanone Structure

1-Methylcyclopentanol Structure

1-Methylcyclope...

5-Chloropentanal Structure

5-Chloropentanal

~%

2,2,3-trimethylheptan-3-ol Structure

2,2,3-trimethyl...

6-Chloro-2-hexanone Structure

6-Chloro-2-hexanone

~%

2,2,3-trimethylheptan-3-ol Structure

2,2,3-trimethyl...

6-chlorohexan-2-ol Structure

6-chlorohexan-2-ol

~%

2,2,3-trimethylheptan-3-ol Structure

2,2,3-trimethyl...

1-iodo-5-hexanone Structure

1-iodo-5-hexanone

Tert-Butyllithium Structure

Tert-Butyllithium

~20%

2,2,3-trimethylheptan-3-ol Structure

2,2,3-trimethyl...

2-Hexanone Structure

Detail

N/A Structure

~69%

Cyclopentanone Structure

Soluble Lanthanide Salts (LnCl3⋅ 2 LiCl) for the Improved Ad...

[Krasovskiy, Arkady; Kopp, Felix; Knochel, Paul Angewandte Chemie - International Edition, 2006 , vol. 45, # 3 p. 497 - 500]

Olefinic Cyclizations. VI. Formolysis of Some Branched-Chain...

[Johnson,W.S.; Owyang,R. Journal of the American Chemical Society, 1964 , vol. 86, p. 5593 - 5598]

The Effect of Cyclopentane and Cyclohexane Rings on the Reac...

[Skinner; Florentine Journal of the American Chemical Society, 1954 , vol. 76, p. 3200,3201]

Olefinic Cyclizations. VI. Formolysis of Some Branched-Chain...

[Johnson,W.S.; Owyang,R. Journal of the American Chemical Society, 1964 , vol. 86, p. 5593 - 5598]

Some studies on the solvolysis of 1-chloro-1-alkyl cycloalka...

[Ranganayakulu, K.; Vasumathi Devi, M.; Balaji Rao, R.; Rajeswari, K. Canadian Journal of Chemistry, 1980 , vol. 58, # 14 p. 1484 - 1489]