3,4:8,9-dibenzo-1-6-metano (10) Anulen`in sentezi için çalışmalar

Abstract

3,4;8,9-DIBENZO-l-6-METANO[lO]ANULEN'İN SENTEZİ İÇİN ÇALIŞMALAR (Yüksek Lisans Tezi) Recep ÖZEN GAZİ ÜNİVERSİTESİ FEN BİLİMLERİ ENSTİTÜSÜ Nisan 1995 oz 5,6,1 1,1 2-telrahidroantrasen'in (12) sentezi, tetra brommetil etilen'in (8) Zn-Cu çini ile eliminasyonundan elde edilen 2,3-bis (brommetil)- 1,3-butadien (9) ile benzin'in katılma ürünü 2,3-bis (brommetil)- 1,4-dihidronaftalin (10), dan dibrom eliminasyonuyla oluşturulan 2,3-dimetilen-l,2,3,4-tetrahidronaftalin'e (11) benzin katarak gerçekleştirildi. 2,3- dimetilen - I, 2, 3, 4 - tetrahidronaftalin'in (11) 2,3 - dimetilnaftalin'e (87) düzenlendiği ve 2,3-bis (brommetil)- 1,4- dihidronaftalin'in ( 1 0) aromatiki eşerek 2,3-bis (brommetil) naftalin'e (86) dönüştüğü belirlendi. Üç ayrı ekzosiklik dien; 2,3-dimetilen- 1,2,3,4- tetrahidronaftalin (11), 2,3-bis (brommetil)- 1,3-butadien (9) ve dimetiI-4,5-bis (brommetil) siklohekza-l,4-dien-l,2-dikarboksilat'ın (100) singlet oksijenle reaksiyonundan oluşan endoperoksitleri 2,3-dioksa-l,4,9,10-tetrahidroantrasen (96), 4,5-bis (brommetil)- 1, 2-dioksasiklohekza-4-en (98) ve dimetil-2,3- dioksa-6,7-dikarboksilat- 1,4,5,8-tetrahidronaftalin'in (102) düzenlenme ürün leri furanlar; sırasıyla l,2,3,4-tetrahidronafto[b]furan (97), 3,4-bis (brommetil) furan (99) ve dimetil- 1,2-furano-4-siklohekzen-4,5-dikarboksilat (103) elde edildi.

THE STUDIES ON 3,4:8,9-DIBENZO-l-6-METIIANO[lO] ANNULEN (M. Sc. Thesis) Recep ÖZEN GAZI UNIVERSITY INSTITUTE OF SCIENCE AND TECHNOLOGY April 1995 ABSTRACT 5,6,1 1,1 2-tetrahydroanthracane (12) was synthesized from the cyclo addition reaction of benzyne and 2,3-dimethylene-l,2,3,4-tetrahydronaphtalane (11) which was obtained by the elimination reaction from the 2,3- bis(bromomethyl)-l,4-dihydronaphta1ane (10) prepared from the cycloaddition reaction of benzene and 2,3-bis(bromomethyI)-l,3-butadiene (9) obtained from tetrabromomethylene by the elimination reaction with Zn-Cu couple. 2,3- dimethylene-l,2,3,4-tetrahydronaphtalane (II) was rearranged to 2,3- dimethylnaphtalane (87) to 2,3 bis(bromomethyl) naphtalane (86). 1,2,3,4- tetrahydronaphto[b]furan (97), 3,4-bis(bromomethyl) furan (99) and dimethyl- l,2-furano-4-cyclohexene-4,5-dicarboxylate (103) was obtained respectively from the rearrangementof the endoperoxides 2,3-dioxa- 1,4,9, 10- tetrahydroantracane (96), 4,5-bis(bromomethyl)-l,2-dioxacyclohexa-4-en (98) and dirnethyl-2,3-dioxa-6,7-dicarboxylate-l,4,5,8-tetrahydronaphtaIane (102) which were synthesized respectively three exocyclic dienes 2,3-dimethylene- 1,2,3,4-tetrahydronaphtalane (11), 2,3-bis(bromomethyl)-l,3-butadiene (9) and dimethyl-4,5-bis(bromomethyl) cyclohexa- 1,4-diene- 1,2-dicarboxylate (100). II