Health & Environmental Research Online (HERO)


Print Feedback Export to File
3536935 
Journal Article 
Vicinally substituted cyclopentenes and cyclopentenones from (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
Akhmet'yanova, VA; Ivanova, NA; Valiullina, ZR; Miftakhov, MS 
2015 
1 
Russian Journal of Organic Chemistry
ISSN: 1070-4280
EISSN: 1608-3393 
Maik Nauka Publishing / Springer SBM 
51 
3 
319-324 
English 
WOS:000352908800005 
Solvolysis of (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6 one in a mixture of tert-butyl alcohol with water and triethylamine, followed by successive
treatment with K2CO3, NaBH4, and CH2N2, gave methyl 2-(hydroxymethyl)cyclopent-2-ene-1-
carboxylate which was subjected to hydride reduction, epoxidation, trichloroacetimidation, and
acetylation. Allylic oxidation of methyl 2-(acetoxymethyl)cyclopent-2-ene-1-carboxylate with the
chromium(VI) oxide-3,5-dimethylpyrazole complex afforded methyl 2-(acetoxymethyl)-4-
oxocyclopent-2-ene-1-carboxylate, and methyl (1R*,2R*,5R*)-1-(hydroxymethyl)-6-oxabicyclo
[3.1.0]-hexane-2-carboxylate was converted into a building block for the synthesis of
deoxyentecavir and sarcomycine methyl ester. 
IRIS
• tert-Butanol
     Excluded/ Not on Topic
          Chemical Analysis/Fuel Chemistry