ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Trimethyl bicyclobutane-1,2,2-tricarboxylate (2) was synthesized by a facile five-step route, beginning with the ferric chloride-catalyzed addition of chloroform to methyl acrylate to give methyl 2,4,4-trichlorobutyrate (3). Replacement of the 2-chloro group by iodide was followed by displacement with dimethyl malonate anion to give trimethyl 4,4-dichlorobutane-1,1,2-tricarboxylate (5a). Thermolysis of the corresponding sodium derivative 5b gave trimethyl cis, trans-3-chlorocyclobutane-1,2,2-tricarboxylate (6). Closure of the bicyclobutane ring to yield 2 was accomplished by potassium hydride in ether with methanol as catalyst.Bicyclobutane 2 polymerized under free radical initiation with breakage only of the 1,3-bond. The homopolymers, obtained in moderate yields, were of low molecular weight, probably owing to steric hindrance effects. Copolymerization occurred with vinyl monomers of varying polarity. The copolymers, obtained in moderate yields, had low molecular weights and consisted mostly of the vinyl comonomer units.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19770600608
