Synthesis and trapping of spiro [bicyclo[4.2.0]octa-2,3-diene-7,2'-[1,3]dioxolane]

Mustafa Ceylan; Esra Koç

Makale detayları

Synthesis and trapping of spiro [bicyclo[4.2.0]octa-2,3-diene-7,2'-[1,3]dioxolane]

Yazarlar:

Mustafa Ceylan | Esra Koç

Yayıncı:

Tokat Gaziosmanpasa University

Ana Başlıklar:

Organic Chemical Synthesis

Dergi:

Journal of New Results in Science Vol.12 Issue 3, pp.131-138

Belge Tipi:

Makale

Yayın Tarihi:

12/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001309078

pISSN:

1304-7981

Anahtar kelimeler:

Özet:

 Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane was synthesized by the reaction of bicyclo3.2.0hept-2-en-6-one with ethylene glycol in yield of 92. Addition of dichlorocarbene to Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane gave the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane in 50  yields. Finally, the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane was submitted to Doering-Moore-Skatebol reaction for the synthesis of allene precursors. The reaction of the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4 octane with methyl lithium MeLi in the presence of 1,3-diphenylisobenzofuran DBI as a trapping reagent under a nitrogen atmosphere at ca. 0  was started and continued at room temperature for four hours, resulting in the formation of four cyclo adduct isomers of spirobicyclo4.2.0octa-2,3-diene-7,2-1,3dioxolane.

 Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane was synthesized by the reaction of bicyclo3.2.0hept-2-en-6-one with ethylene glycol in yield of 92. Addition of dichlorocarbene to Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane gave the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane in 50  yields. Finally, the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane was submitted to Doering-Moore-Skatebol reaction for the synthesis of allene precursors. The reaction of the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4 octane with methyl lithium MeLi in the presence of 1,3-diphenylisobenzofuran DBI as a trapping reagent under a nitrogen atmosphere at ca. 0  was started and continued at room temperature for four hours, resulting in the formation of four cyclo adduct isomers of spirobicyclo4.2.0octa-2,3-diene-7,2-1,3dioxolane.

 Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane was synthesized by the reaction of bicyclo3.2.0hept-2-en-6-one with ethylene glycol in yield of 92. Addition of dichlorocarbene to Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane gave the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane in 50  yields. Finally, the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane was submitted to Doering-Moore-Skatebol reaction for the synthesis of allene precursors. The reaction of the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4 octane with methyl lithium MeLi in the presence of 1,3-diphenylisobenzofuran DBI as a trapping reagent under a nitrogen atmosphere at ca. 0  was started and continued at room temperature for four hours, resulting in the formation of four cyclo adduct isomers of spirobicyclo4.2.0octa-2,3-diene-7,2-1,3dioxolane.

 Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane was synthesized by the reaction of bicyclo3.2.0hept-2-en-6-one with ethylene glycol in yield of 92. Addition of dichlorocarbene to Spirobicyclo3.2.0hept-2-ene-6,2-1,3dioxolane gave the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane in 50  yields. Finally, the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4octane was submitted to Doering-Moore-Skatebol reaction for the synthesis of allene precursors. The reaction of the 3,3-Dichlorospiro1,3-dioxolane-2,7-tricyclo4.2.0.02,4 octane with methyl lithium MeLi in the presence of 1,3-diphenylisobenzofuran DBI as a trapping reagent under a nitrogen atmosphere at ca. 0  was started and continued at room temperature for four hours, resulting in the formation of four cyclo adduct isomers of spirobicyclo4.2.0octa-2,3-diene-7,2-1,3dioxolane.

Makale detayları

Synthesis and trapping of spiro [bicyclo[4.2.0]octa-2,3-diene-7,2'-[1,3]dioxolane]

Yazarlar:

Mustafa Ceylan | Esra Koç

Yayıncı:

Tokat Gaziosmanpasa University

Ana Başlıklar:

Organic Chemical Synthesis

Dergi:

Journal of New Results in Science Vol.12 Issue 3, pp.131-138

Belge Tipi:

Makale

Yayın Tarihi:

12/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001309078

pISSN:

1304-7981

Allene

1,2-Cyclohexadiene

Carbene

Doering-Moore-Skatebol reaction

Sayı

Makale detayları

Synthesis and trapping of spiro [bicyclo[4.2.0]octa-2,3-diene-7,2'-[1,3]dioxolane]

Yazarlar: Mustafa Ceylan | Esra Koç

Yayıncı: Tokat Gaziosmanpasa University

Ana Başlıklar: Organic Chemical Synthesis

Dergi: Journal of New Results in Science Vol.12 Issue 3, pp.131-138

Belge Tipi: Makale

Yayın Tarihi: 12/2023

Belge Dili: İngilizce

Document ID (Org No.): 2001309078

pISSN: 1304-7981

Allene

1,2-Cyclohexadiene

Carbene

Doering-Moore-Skatebol reaction

Sayı

Yazarlar:

Mustafa Ceylan | Esra Koç

Yayıncı:

Tokat Gaziosmanpasa University

Ana Başlıklar:

Organic Chemical Synthesis

Dergi:

Journal of New Results in Science Vol.12 Issue 3, pp.131-138

Belge Tipi:

Makale

Yayın Tarihi:

12/2023

Belge Dili:

İngilizce

Document ID (Org No.):

2001309078

pISSN:

1304-7981