Structural studies on cycloadducts of furan, 2-methoxyfuran, and 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide.
The early stages of the retro-Diels-Alder reaction are clearly apparent in the structures of the cycloadducts formed between furan or 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide. The degree of lengthening of the C-C bonds that break in this reaction is clearly related to the known reactivity of these cycloadducts toward this reaction. In the structures of the cycloadducts 21 and 22 derived from 2-methoxyfuran, the early stages of an alternative fragmentation reaction are apparent, consistent with the reactivity of these compounds in solution.
Goh
Yit Wooi
YW
School of Chemistry and Bio-21 Institute, The University of Melbourne, Parkville Vic 3010, Australia.
Pool
Brett R
BR
White
Jonathan M
JM
D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008299:Maleic Anhydrides / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
C527324:5-trimethylsilylcyclopentadiene; D003517:Cyclopentanes; D005663:Furans; D008299:Maleic Anhydrides; D008301:Maleimides; C527323:N-methylmaleimide