Beilstein J. Org. Chem.2009,5, No. 39, doi:10.3762/bjoc.5.39
Bilal Nisanci Erdin Dalkilic Murat Guney Arif Dastan Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum-TURKEY 10.3762/bjoc.5.39 Abstract Dimeric forms of norbornadiene and benzonorbornadiene were synthesized starting with known monobromide derivatives. The Diels–Alder
cycloaddition reaction of dimers with TCNE and PTAD was investigated and new norbornenoid polycyclics were obtained. All compounds were characterized properly using NMR spectroscopy.
Keywords: benzonorbornadiene; Diels–Alder reaction; norbornadiene; Stille coupling; Introduction
Norbornadiene (1) and related
rearrangement [12][13][14][15], as well as in other instances [16][17][18][19][20][21][22]. Therefore, functionalizations of these compounds are important. In this study, we investigated the synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers.
Results and Discussion
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Graphical Abstract
Scheme 1:
Synthesis of starting materials 4 and 5.
Beilstein J. Org. Chem.2005,1, No. 3, doi:10.1186/1860-5397-1-3
precursor Rh(nbd)2BF4 (nbd = norbornadiene) was treated with the ligands to form pre-catalysts of the type RhL2(nbd)BF4 and free nbd. Dichloromethane served as the solvent.
In the case of the hydrogenation of the allylic alcohol 1, 21 of the 23 ligands were employed, which means a total of 210 different