ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Does [6+4] Cycloaddition between Pentafulvene and Cyclopentadiene Take Place?Reaction of a 1:1 mixture of cyclopentadiene (CPD) and pentafulvene (1a) at 20° gives a complex mixture. The low-molecular-weight part mainly consists of pure and mixed dimers (ca. 73 %) besides corresponding trimers (ca. 20%) and some corresponding oligomers according to GC/MS investigations (Fig. 1). The 3 predominant ‘mixed dimers’ between CPD and 1a have been separated, and structures 4-6 (Scheme 3) are assigned according to 400- and 600-MHz 1H-NMR investigations. These results show that HOMO(CPD)-LUMO(fulvene) interactions are important in pentafulvene cycloadditions. Dimer 6 results from [6+4] cycloaddition followed by [1,5]-H shifts.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730817
