Uncommon C1-C2 rupture in Methyl-4-C-allyl-2,4-dideoxy-3-O-mesyl-α-D-arabino-hexopyranoside

Russian Journal of Organic Chemistry -     

Some features of RuCl3-catalyzed periodate oxidation of 3-N-substituted 5-allenyl-2,5-dichloro-4,4-dimethoxycyclopent-2-en-1-ones

3-N-Substituted 5-(1Z-carboxymethylene)-2-chloro-4,4-dimethoxycyclopent-2-en-1-ones have been prepared from the corresponding 3-N-substituted 5-allenyl-2,5-dichloro-4,4-dimethoxycyclopent-2-en-1-ones using selective oxidative cleavage of their allene bond by the RuCl₃−NaIO₄ system. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1646–1648, September, 1997.     

Reaction of 5-allyl-2,5-dichloro-4,4-dimethoxy-3-morpholinocyclopent-2-enone with Me3SiI

5-Allyl-2,5-dichloro-4,4-dimethoxy-3-morpholinocyclopent-2-enone reacts with Me₃SiI in MeCN to give the corresponding product of reductive vinylic monodechlorination. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1660–1661, August, 1998.     

Formation of isomeric iodohydrins from terminal alkenes upon oxidation by a RuCl3-NaIO4 system

RuCl₃-catalyzed periodate oxidation of alkenes affords isomeric iodohydrins.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2961–2963, December, 1996.     

Reactions of secondary amines with derivatives of 5-(2-methyl-3-furyl)cyclopent-2-en-1-one

The reactions of 2,3,5-trichloro- and 2,5-dichloro-3-furfuryloxy-5-(2-methyl-3-furyl)-4,4-dimethoxycyclopent-2-en-1-ones with diethylamine or morpholine result in the decyclization of the 2-methylfuran substituent, giving the corresponding products in good yields.     

New chlorinated cyclopentenones prepared from hexachlorocyclopentadiene: synthesis,chemical properties,and application in the synthesis

The review surveys chemical conversions of 5-substituted 2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-ones and related compounds and the possibilities of their use in the synthesis.