Manganese(III) Acetate Mediated Free Radical Cyclization of 1,3-Dicarbonyl Compounds with Sterically Hindered Olefins

Mehmet YILMAZ; Emre BİÇER and A. Tarık PEKEL

Article Details

Manganese(III) Acetate Mediated Free Radical Cyclization of 1,3-Dicarbonyl Compounds with Sterically Hindered Olefins

Authors:

Mehmet YILMAZ | Emre BİÇER and A. Tarık PEKEL

Publisher:

TUBITAK

Journal:

Turkish Journal of Chemistry 2005 Vol.29 Issue 6, pp.579-587

Document Type:

Article

Publication Date:

5/2005

Document Language:

Turkish

Document ID (Org No.):

2000728981

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

Abstract:

 

The manganese(III) acetate mediated radical cyclization of  dimedone 1a, 2,4-pentanedione 1b, ethyl acetoacetate 1c,  1,3-cyclohexanedione 1d and 5-phenyl-1,3-cyclohexanedione 1e with  1,1-diphenyl-1-butene 2a afforded 4,5-dihydrofurans (3c, 3e) and  tetrahydrobenzofurans (3a, 3g, 3h) in good yields (55% - 77%).   Additionally, the reactions of trifluoromethyl-group containing  1,3-dicarbonyls, 4,4,4-trifluoro-1-phenylbutane-1,3-dione 1f and  4,4,4-trifluoro-1-thien-2ylbutane-1,3-dione 1g with 2a  3-trifluoroacetyl-4,5-dihydrofurans gave in 74% and 78% yields,  respectively.  Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene  2a resulted in the formation of tetrahydrobenzofuran 3b and  4,5-dihydrofurans 3d and 3f in lower yields.

 

The manganese(III) acetate mediated radical cyclization of  dimedone 1a, 2,4-pentanedione 1b, ethyl acetoacetate 1c,  1,3-cyclohexanedione 1d and 5-phenyl-1,3-cyclohexanedione 1e with  1,1-diphenyl-1-butene 2a afforded 4,5-dihydrofurans (3c, 3e) and  tetrahydrobenzofurans (3a, 3g, 3h) in good yields (55% - 77%).   Additionally, the reactions of trifluoromethyl-group containing  1,3-dicarbonyls, 4,4,4-trifluoro-1-phenylbutane-1,3-dione 1f and  4,4,4-trifluoro-1-thien-2ylbutane-1,3-dione 1g with 2a  3-trifluoroacetyl-4,5-dihydrofurans gave in 74% and 78% yields,  respectively.  Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene  2a resulted in the formation of tetrahydrobenzofuran 3b and  4,5-dihydrofurans 3d and 3f in lower yields.

Article Details

Manganese(III) Acetate Mediated Free Radical Cyclization of 1,3-Dicarbonyl Compounds with Sterically Hindered Olefins

Authors: Mehmet YILMAZ | Emre BİÇER and A. Tarık PEKEL

Publisher: TUBITAK

Journal: Turkish Journal of Chemistry 2005 Vol.29 Issue 6, pp.579-587

Document Type: Article

Publication Date: 5/2005

Document Language: Turkish

Document ID (Org No.): 2000728981

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

Issues

Authors:

Mehmet YILMAZ | Emre BİÇER and A. Tarık PEKEL

Publisher:

TUBITAK

Journal:

Turkish Journal of Chemistry 2005 Vol.29 Issue 6, pp.579-587

Document Type:

Article

Publication Date:

5/2005

Document Language:

Turkish

Document ID (Org No.):

2000728981

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527