98361-39-8Relevant academic research and scientific papers
Lewis acid-promoted rearrangement of 2,3-epoxy alcohol derivatives: Stereochemical control and selective formation of two types of chiral quaternary carbon centers from the single carbon skeleton
Kita, Yasuyuki,Matsuda, Satoshi,Inoguchi, Ryoko,Ganesh, Jnaneshwara K.,Fujioka, Hiromichi
, p. 5191 - 5197 (2007/10/03)
The Lewis acid-promoted rearrangement of 2,2,3,3-tetrasubstituted 2,3-epoxy alcohols with several kinds of protecting groups was investigated. When SnCl4 is used as a Lewis acid, the reaction proceeds in a regio- and stereo-controlled manner to
Hypervalent iodine(III) reagent-promoted rearrangement and subsequent oxidative ring cleavage of cyclic 2,3-epoxy-1-alcohol derivatives
Kita, Yasuyuki,Matsuda, Satoshi,Fujii, Eri,Kitagaki, Shinji,Inoguchi, Ryoko,Hata, Kayoko,Fujioka, Hiromichi
, p. 309 - 317 (2007/10/03)
The rearrangements of 2,3-epoxy alcohol derivatives were achieved using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). In the case of 2,3-epoxy alcohols subsequent oxidative ring cleavage occurred to give ω-formylalka
Acid-promoted rearrangement of cyclic α,β-epoxy acylates: Stereoselective synthesis of spirocyclanes and quaternary carbon centers
Kita, Yasuyuki,Kitagaki, Shinji,Yoshida, Yutaka,Mihara, Sachiko,Fang, Dai-Fei,Kondo, Michinori,Okamoto, Sachi,Imai, Reiko,Akai, Shuji,Fujioka, Hiromichi
, p. 4991 - 4997 (2007/10/03)
The rearrangement reaction of α,β-epoxy acylates in cyclic systems was studied. The treatment of cis-derivatives with a Lewis acid afforded rearranged products via the regioselective β-cleavage of the oxirane ring due to the electron-withdrawing nature of the acyloxy group, whereas trans- derivatives enhanced the neighboring group participation to yield only a small amount of rearranged products. This rearrangement reaction proved to be useful for the construction of a variety of spirocyclane systems or quaternary carbon centers on rings and could be applied to their syntheses as optically active forms.
THE INFLUENCE OF HYDROGEN BONDING ON THE SOLVOLYTIC REACTIVITY OF NICOTINATES IN FLUORINATED ALCOHOLS
Jursic, Branko,Sunko, Dionis E.,Ladika, Mladen
, p. 4367 - 4376 (2007/10/02)
A systematic investigation of solvolytic reactivities of allylic and benzylic nicotinates and their N-methylated derivatives in 80percent EtOH, 97percent TFE and 97percent HFIP was undertaken.The nicotinates in 97percent HFIP are slightly more reactive th
SOLVOLYSIS OF 2-(ω-ALKOXYALKYL)-3-METHYL-2-CYCLOHEXENYL p-NITROBENZOATES. SEARCH FOR NEIGHBORING OXYGEN PARTICIPATION
Ladika, Mladen,Jursic, Branko,Sunko, Dionis E.
, p. 179 - 190 (2007/10/02)
The degree of alkoxy group participation in the solvolysis of allylic p-nitrobenzoates with an ω-alkoxyalkyl side-chain at C-2 center was studied.In 80 percent EtOH the solvolysis rates, secondary α-deuterium isotope effects, and the product composition s
NEIGHBORING SULFUR PARTICIPATION IN THE SOLVOLYSIS OF 2-(ω-ALKYLTHIOALKYL)-3-METHYL-2-CYCLOHEXENYL p-NITROBENZOATES
Ladika, Mladen,Jursic, Branko,Mihalic, Zlatko,Sunko, Dionis E.
, p. 1703 - 1706 (2007/10/02)
As shown by kinetic and product analysis, the solvolysis of 7 and 8 in 97percent TFE includes several competitive reactions, one of them being neighboring sulfur participation and formation of intermediate cyclic sulfonium cation.
Solvolysis of 2-Alkenyl-2-cyclohexenyl p-Nitrobenzoates
Ladika, Mladen,Sunko, Dionis E.
, p. 4544 - 4548 (2007/10/02)
In an attempt to study possible ?-participation in allyl derivatives, 2-alkenyl-3-methyl-2-cyclohexenyl p-nitrobenzoates 6 and 7 were solvolyzed in 97 wt percent trifluoroethanol and 80 vol percent ethanol.These esters show in both solvents a solvolysis r
