ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
[2+4]-Cycloaddition Products of 3,4-Dimethoxyfuran with Acetylenedicarboxylates and Their Transformations under the Influence of Rhodium(I) Catalysts3,4-Dimethoxyfuran (1) readily reacts with acetylenedicarboxylates (2) at room temperature in a [2+4]-cycloaddition to give a mono-(3) and several di-addition products. 90% of the latter consists of the endo-exo compound 4. Under the influence of catalytic amounts of [Rh(CO)2Cl]2 the mixture of mono- and di-adducts in methanolic solution is smoothly transformed into endo-5,5,6-trimethoxy-7-oxabicyclo [2.2.1]hept-2-ene-2,3-dicarboxylateAlle Verbindungen sind racemisch. Die Formeln stellen jeweils nur ein Enantiomeres dar. (5) , 3-hydroxy-4,5-dimethoxyphthalate ( 6) and (I R*, 2 S*, 4 R*, 5 R*, 7 R*, 11 R*, 12 R*) -5,8,8,9,12-pentamethoxy-3,6-dioxatetracyclo [5.3.1.1 2,5 . 0 4,11]dodec-9-ene-1,11-dicarboxylate ( 7).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19780610327
