1-siklohept-1,2-dien-1-ilbenzen?in [4+2] katılma ve [2+2] dimerleşme ürünlerinin sentezi

Abstract

Bu çalışmada, 1-(2-klorosiklohept-1-en-1-il)benzen (48) ve 1-(2-klorosiklohept-2-en-1-il)benzen (49)'den çıkılarak, 1-siklohept-1,2-dien-1-ilbenzen'in (18) sentezi üzerineçalışıldı.Öncelikle, 2-fenilsikloheptanon'un PCl5 ile reaksiyonundan başlangıç bileşikleri olan 48ve 49 sentezlendi.Ph Ph PhO Cl ClPCl5+CCl450 48 49İkinci aşamada, çıkış bileşikleri 48 ve 49'un kapalı tüp ve 1850C'de KOtBu ilereaksiyonları incelendi. Her iki reasiyonda da HCl eliminasyonu ile oluşan 1-siklohept-1,2-dien-1-ilbenzen'in (18) dimerleşme ürünleri olan 51 ve 52 izole edildi.PhClKapali tüp PhKOt-Bu/Benzen1850C48 +Ph PhPhCl 1828Kapali tüp 27KOt-Bu/Benzen1850C49İlave olarak; vinil klorürler 48 ve 49'un aynı şartlarda, DBI varlığında KOtBu ilereaksiyonları araştırıldı. Bu reaksiyonlardan da, 1-siklohept-1,2-dien-1-ilbenzen'in (39)DBI ile [4+2] katılma ürünleri 57 ve 58 izole edildi.PhPhCIKapalı tüp 57OPhKOtBu / Benzen PhDBI,1850C48 PhPhPhCIKapalı tüp 58O18KOtBu / BenzenPhDBI,1850CPh49Anahtar Kelimeler:Allen, dimerleşme, dehidrohalojenasyon, 1-Siklohept-1,2-dien-1-ilbenzen.

In this study, the synthesis of 1-cyclohept-1,2-dien-1-ylbenzene (18) from vinyl clorides,1-(2-chlorocyclohept-1-en-1-yl)benzene (48) and 1-(2-chlorocyclohept-2-en-1-yl)benzene (49), was studied.Fistly, the starting compounds, 1-(2-chlorocyclohept-1-en-1-yl)benzene (48) and 1-(2-chlorocyclohept-2-en-1-yl)benzene (49), were synthesized from the reaction of 2-phenylcycloheptanone (50) with PCl5 .Ph Ph PhO Cl ClPCl5+CCl450 48 49Secondly, the reactions of the starting compounds 48 and 49 with KOtBu in sealed tube,at 1850C were examined. [2+2] Dimerization products 51 and 52 of 1-cyclohept-1,2-dien-1-ylbenzene 18 were isolated from the each reactions.PhClSealed tube PhKOt-Bu/Benzene1850C48 +Ph PhPhCl 1828Sealed tube 27KOt-Bu/Benzene1850C49Additionaly; in the same conditions, the reactions of vinyl clorides 48 and 49 withKOtBu in the presence of DBI were investigated. [4+2] Addition products, 57 and 58, of1-cyclohept-1,2-dien-1-ylbenzene (18) with DBI were isolated from the each reactions.PhPhCI57Sealed tube OPhKOtBu / BenzenePhDBI,1850C48 PhPhPhCISealed tube 39 58OKOtBu / Benzene PhDBI,1850C49 PhKey Words:Allene, dimerization, dehydrohalogenation, 1-Cyclohept-1,2-dien-1-ylbenzene.