ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A meta-Xylylene by Bamford-Stevens Reaction of a Fulvene-Ketene-AdductHeating the sodium salt 8 of the tosylhydrazone 4 of 4-isopropyliden-7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one (3; obtained by the addition of dimethylketene to 6,6-dimethylfulvene (1)), in diglyme at 130° led to the cotamethyl-[2.2]metacyclophane 10 (17%). The latter probably was formed by dimerization of the non-Kékulé molecule m-xylylene 14, which, in turn, could have arisen via the homofulvene 13 from the carbene 12. A second product in the thermolysis of 8 was the tricycle 9 (9 %), as a result of an intramolecular insertion of the carbene C-atom in 12 into a methyl C,H-bond. Further products were the azines 11a, 11b (50%), of the type known as byproducts in Bamford-Stevens reactions. Heating dry 8 afforded 9 (9%) and the two benzene derivatives 15 (9%) and 16 (3%). The tosylhydrazone 4 could be recovered by reaction of 11a, 11b with p-toluenesulfonohydrazide.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19840670525
