PSEUDOESTERS AND DERIVATIVES .33. SYNTHES IS OF CYCLOPROPANE DERIVATIVES BY PHOTOLYSIS OF PYRAZOLINES OBTAINED BY 1,3-DIPOLAR CYCLOADDITIONTO 5-METHOXY-2(5H)-FURANONE

Authors
FARIA F MARTIN MV SORIA ML
Citation
F. Faria et al., PSEUDOESTERS AND DERIVATIVES .33. SYNTHES IS OF CYCLOPROPANE DERIVATIVES BY PHOTOLYSIS OF PYRAZOLINES OBTAINED BY 1,3-DIPOLAR CYCLOADDITIONTO 5-METHOXY-2(5H)-FURANONE, Anales de quimica, 91(1-2), 1995, pp. 65-73
Citations number
47
Categorie Soggetti
Chemistry
Journal title
Anales de quimica → ACNP
ISSN journal
11302283
Volume
91
Issue
1-2
Year of publication
1995
Pages
65 - 73
Database
ISI
SICI code
1130-2283(1995)91:1-2<65:PAD.SI>2.0.ZU;2-D
Abstract
By cycloaddition of 2-diazopropane to 5-methoxy-2(5H)-furanone (1) two regioisomeric 1-pyrazolines 3 and 4 are stereospecifically obtained. Both isomers give by photolysis, as major or sole compound, the same c yclopropane derivative 7. Hydrolysis of the bicyclic compound 7, follo wed by esterification, leads to cis open chain derivatives, which are appropriately functionalized for the synthesis of pyrethroids. A simil ar set of reactions, using diazomethane-d(2) as dipolarophile, affords selectively deuterated cyclopropane derivatives.