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

Free-radical macrocyclization-transannular cyclization

NA Porter, VHT Chang, DR Magnin…

Index: Porter,N.A.; Chang,V.H.; Magnin,D.R. Journal of the American Chemical Society, 1988 , vol. 110, p. 3554

Full Text: HTML

Citation Number: 87

Abstract

Abstract: Intramolecular free-radical addition to olefins substituted with electron-withdrawing groups has been studied. The free radicals are generated from the corresponding iodides by reaction with tributyltin hydride or tributyltin chloride/sodium cyanoborohydride. Macrocyclic compounds of 12-20 members are generated by this procedure in good yield, while endocyclization is favored, exocyclization can be forced if 1, l-dicyanesubstituted olefins ...

16-Bromo-1-hexadecanol Structure

16-Bromo-1-hexa...

~%

Cyclooctadecanone Structure

Cyclooctadecanone

16-bromohexadecanal Structure

16-bromohexadecanal

~%

Cyclooctadecanone Structure

Cyclooctadecanone

10-iododec-1-en-3-one Structure

10-iododec-1-en...

~15%

CYCLODECANONE Structure

3-decanone Structure

dec-1-en-3-one Structure

Detail

10-iododec-1-en-3-one Structure

10-iododec-1-en...

~0%

CYCLODECANONE Structure

3-decanone Structure

dec-1-en-3-one Structure

Detail

8-Bromooctanol Structure

~%

dec-1-en-3-one Structure

8-Bromooctanal Structure

~%

dec-1-en-3-one Structure

10-bromodec-1-en-3-ol Structure

10-bromodec-1-e...

~%

dec-1-en-3-one Structure

10-iododec-1-en-3-one Structure

10-iododec-1-en...

~0%

CYCLODECANONE Structure

3-decanone Structure

dec-1-en-3-one Structure

Detail

8-Bromooctanol Structure

~%

10-iododec-1-en-3-one Structure

10-iododec-1-en...

8-Bromooctanal Structure

~%

10-iododec-1-en-3-one Structure

10-iododec-1-en...

10-bromodec-1-en-3-ol Structure

10-bromodec-1-e...

~%

10-iododec-1-en-3-one Structure

10-iododec-1-en...

12-Bromo-1-dodecanol Structure

12-Bromo-1-dodecanol

~%

cyclotetradecanone Structure

cyclotetradecanone

12-bromododecanal Structure

12-bromododecanal

~%

cyclotetradecanone Structure

cyclotetradecanone

N/A Structure

~%

cyclotetradecanone Structure

cyclotetradecanone

14-bromo-1-tetradecen-3-one Structure

14-bromo-1-tetr...

~%

cyclotetradecanone Structure

cyclotetradecanone

14-iodo-1-tetradecen-3-one Structure

14-iodo-1-tetra...

~%

3-Tetradecanone Structure

3-Tetradecanone

tetradec-1-en-3-one Structure

tetradec-1-en-3-one

cyclotetradecanone Structure

cyclotetradecanone

16-Bromo-1-hexadecanol Structure

16-Bromo-1-hexa...

~%

3-OCTADECANONE Structure

16-bromohexadecanal Structure

16-bromohexadecanal

~%

3-OCTADECANONE Structure

Photoinduced Electron Transfer Promoted Radical Ring Expansi...

[Nishikawa, Keisuke; Yoshimi, Yasuharu; Maeda, Kousuke; Morita, Toshio; Takahashi, Ichiro; Itou, Tatsuya; Inagaki, Sho; Hatanaka, Minoru Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 582 - 589]

Many-membered Carbon Rings. X. Reduction of Diametric Diketo...

[Blomquist et al. Journal of the American Chemical Society, 1955 , vol. 77, p. 1804]

Photoinduced Electron Transfer Promoted Radical Ring Expansi...

[Nishikawa, Keisuke; Yoshimi, Yasuharu; Maeda, Kousuke; Morita, Toshio; Takahashi, Ichiro; Itou, Tatsuya; Inagaki, Sho; Hatanaka, Minoru Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 582 - 589]

Photoinduced Electron Transfer Promoted Radical Ring Expansi...

[Nishikawa, Keisuke; Yoshimi, Yasuharu; Maeda, Kousuke; Morita, Toshio; Takahashi, Ichiro; Itou, Tatsuya; Inagaki, Sho; Hatanaka, Minoru Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 582 - 589]

Photoinduced Electron Transfer Promoted Radical Ring Expansi...

[Nishikawa, Keisuke; Yoshimi, Yasuharu; Maeda, Kousuke; Morita, Toshio; Takahashi, Ichiro; Itou, Tatsuya; Inagaki, Sho; Hatanaka, Minoru Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 582 - 589]