Synthesis of 1-Cyclohept-1,2-dien-1-yl Benzene from 1-(2-iodo-, chlorocyclohept-1-en-1-yl)benzene and 1-(2-iodo-, chlorocyclohept-2-en-1-yl)benzene: Its Trapping with Diphenylisobenzofuran

Mustafa CEYLAN; Yakup BUDAK; Murat ULUKAYA

Article Details

Synthesis of 1-Cyclohept-1,2-dien-1-yl Benzene from 1-(2-iodo-, chlorocyclohept-1-en-1-yl)benzene and 1-(2-iodo-, chlorocyclohept-2-en-1-yl)benzene: Its Trapping with Diphenylisobenzofuran

Authors:

Mustafa CEYLAN | Yakup BUDAK | Murat ULUKAYA

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2006 Vol.30 Issue 6, pp.663-672

Document Type:

Article

Publication Date:

5/2006

Document Language:

English

Document ID (Org No.):

2000728802

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

Abstract:

 

The key compounds vinyl iodides 12a and 13a, for the  generation of 1-cyclohept-1,2-dien-1-ylbezene (1), were synthesized  from cycloheptanone (5).  Bromobenzene was converted to the Grignard  reagent, which was condensed with 5.  Dehydration of alcohol 6 gave  alkene 7.  Hydroboration of 7 followed by oxidation with PCC afforded  ketone 9, which was converted to hydrazone 10.  Treatment of 10 with  iodine resulted in the formation of 12a and 13a.  The other  precursors, 12b and 13b, were synthesized from the reaction of 9 with  PCl5.  Reactions of 12a, b and 13a, b with KOtBu in a sealed tube at  185 °C gave the [2+4] and [2+2] dimer products 20 and 21,  respectively.  In addition, reactions of 12a, b and 13a, b with KOtBu  under the same conditions in the presence of diphenylbenzoisofuran  (DBI) as a trapping reagent afforded the [2+4] cycloadducts 24 and 25  in good yields.

 

The key compounds vinyl iodides 12a and 13a, for the  generation of 1-cyclohept-1,2-dien-1-ylbezene (1), were synthesized  from cycloheptanone (5).  Bromobenzene was converted to the Grignard  reagent, which was condensed with 5.  Dehydration of alcohol 6 gave  alkene 7.  Hydroboration of 7 followed by oxidation with PCC afforded  ketone 9, which was converted to hydrazone 10.  Treatment of 10 with  iodine resulted in the formation of 12a and 13a.  The other  precursors, 12b and 13b, were synthesized from the reaction of 9 with  PCl5.  Reactions of 12a, b and 13a, b with KOtBu in a sealed tube at  185 °C gave the [2+4] and [2+2] dimer products 20 and 21,  respectively.  In addition, reactions of 12a, b and 13a, b with KOtBu  under the same conditions in the presence of diphenylbenzoisofuran  (DBI) as a trapping reagent afforded the [2+4] cycloadducts 24 and 25  in good yields.

Article Details

Synthesis of 1-Cyclohept-1,2-dien-1-yl Benzene from 1-(2-iodo-, chlorocyclohept-1-en-1-yl)benzene and 1-(2-iodo-, chlorocyclohept-2-en-1-yl)benzene: Its Trapping with Diphenylisobenzofuran

Authors: Mustafa CEYLAN | Yakup BUDAK | Murat ULUKAYA

Publisher: TUBITAK

Main Topics: Applied physics

Journal: Turkish Journal of Chemistry 2006 Vol.30 Issue 6, pp.663-672

Document Type: Article

Publication Date: 5/2006

Document Language: English

Document ID (Org No.): 2000728802

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

Issues

Authors:

Mustafa CEYLAN | Yakup BUDAK | Murat ULUKAYA

Publisher:

TUBITAK

Main Topics:

Applied physics

Journal:

Turkish Journal of Chemistry 2006 Vol.30 Issue 6, pp.663-672

Document Type:

Article

Publication Date:

5/2006

Document Language:

English

Document ID (Org No.):

2000728802

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527