Nonacarbonyldiiron-, pentacarbonyliron-, or hexacarbonylmolybdenum-induced reacions of 4,5-polymethylene-substituted 2-isoxazolines.
スポンサーリンク
概要
- 論文の詳細を見る
The reaction of 4,5-polymethylene-substituted 2-isoxazolines, 3-phenyl-3a,5,6,7a-tetrahydro-4<I>H</I>-pyrano[3,2-<I>d</I>]isoxazole or 3-phenyl-3a,4,5,6a-tetrahydrofuro[3,2-<I>d</I>]isoxazole, with [Fe<SUB>2</SUB>(CO)<SUB>9</SUB>], [Fe(CO)<SUB>5</SUB>], or [Mo(CO)<SUB>6</SUB>] resulted in the formation of 5-hydroxy-1-phenyl-1-pentanone or 4-hydroxy-1-phenyl-1-butanone, <I>via</I> the N–O and C–C bond cleavage of the 2-isoxazoline ring and the subsequent hydrolysis. The similar reaction of 7a-morpholino- and 7a-(1-pyrrolidinyl)-3-phenyl-3a,4,5,6,7,7a-hexahydro-1,2-benzoisoxazoles undergoes the N–O bond cleavage and, the subsequent elimination of the amino group or the C-3a–C-7a bond fission. Although the reaction of 6a-morpholino- and 6a-(1-pyrrolidinyl)-3-phenyl-3a,4,5,6a-tetrahydro-4<I>H</I>-cyclopent[<I>d</I>]isoxazoles with [Mo(CO)<SUB>6</SUB>] undergoes the N–O bond cleavage, and the subsequent elimination of the amino group or the C-3a–C-6a bond fission, the reaction of those 2-isoxazolines with [Fe<SUB>2</SUB>(CO)<SUB>9</SUB>] proceeds very slowly. The mechanisms are proposed for these reactions.
- 公益社団法人 日本化学会の論文
著者
-
Nitta Makoto
Department Of Applied Pharmacology Toyama Medical And Pharmaceutical University
-
Kobayashi Tomoshige
Department Of Chemistry Faculty Of Science Shinshu University
-
Yi Akihiro
Department of Chemistry, School of Science and Engineering, Waseda University
関連論文
- Pharmacological and Immunohistochemical Characterization of a Mouse Model of Acute Herpetic Pain
- Roles of luteinizing hormone/chorionic gonadotropin receptor in anchorage-dependent and -independent growth in human ovarian surface epithelial cell lines
- Norbornadiene-Fused Heterocycles: Syntheses and Cycloaddition Reactions of 2-Aryl-4,7-dihydro-4,7-methano-2H-isoindoles and 4,7-Dihydro-4,7-methanoisobenzofuran
- Neighboring Group Participation by Heteroaromatic Rings : The Wagner-Meerwein Type Skeletal Rearrangement in the Electrophilic Addition Reactions of Norbornadiene-Fused Furans, Pyrroles, and Thiophenes
- Oxidizing Ability of a Series of (Tropon-2-ylimino)pnictoranes (Pnictogen=P, As, Sb, and Bi) toward Some Alcohols
- Synthesis and Properties of α, α-Bis(heteroazulen-3-yl)-1, 4-benzoquinonemethides
- The Effect of Fused Rings on the Spectral and Electrochemical Properties of Bis-Fused 1, 4-Diacetyl-1, 4-dihydropyrazines
- Norbornadiene-Fused Heterocycles : Synthesis of 5,8-Dihydro-5,8-methanophthalazines and Regioselective Ring Cleavage and Skeletal Rearrangement of 6,7-Epoxy-5,6,7,8-tetrahydro-5,8-methanophthalazine 2-Oxides in Trifluoroacetic Acid
- Norbornadiene-Fused Heterocycles : Synthesis and Bromination Reaction of 5,8-Dihydro-5,8-methanoquinoxaline Derivatives
- Cycloadditions of constrained dicyclopropylethylenes and divinylcyclopropanes with tetracyanoethylene.
- Preparation, 1,3-dipolar cycloaddition, and thermal and photochemical reactions of 3,5-exo- and 3,5-endo-7-methylene-4-azateracyclo[4.2.1.0.2,803,5]nona-9-ones.
- Thermal rearrangements of 1,5-dimethyl- and 1,3,5-trimethyl-8-vinyl-6-methylenetricyclo[3.2.1.02,7]oct-3-en-8-ol and their alkoxides.
- Hexacarbonylmolybdenum-induced N-N bond cleavage of pyrazoles. Conversion of 1-acylpyrazoles to pyrimidines.
- Acid-Induced Dimerization Reactions of N-(Diphenylphosphinyl)-2-propenimines Leading to Pyridine Derivatives.
- On the reaction of N-(diphenylphosphinyl)-1-phenylethanimine with aromatic aldehydes giving 4-aryl-2,6-diphenylpyridine derivatives.
- The solvomercuration, bromination, and related reactions of 1,5-dimethyl-6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds.
- On the reaction of N-vinyliminophosphoranes. 9. The synthesis and reaction of N-(1,3,5-cycloheptatrienyl)iminophosphoranes to provide a novel route to 1-azaazulenes.
- Preparation of novel N-vinyl-, N-(1-butylvinyl)-, and N-(1-methyl-1-pentenyl)iminotriphenylphosphoranes and their reactions with .ALPHA.,.BETA.-unsaturated ketones.
- The preparation and photoreation of spiro(oxirane-2,6'-tricyclo(3.2.1.02,7)oct(3)en)-8'-ones. An intramolecular cycloaddition of photochemically generated ketene with the epoxide ring.
- Photocycloadditions of benzophenone with 6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds. Di-.PI.-methane photorearrangement of the primary photocycloadducts.
- Stereoelectronic and homoconjugative effect of stereoselectivity. The addition of dichlorocarbene to 1,5-dimethyl-6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds.
- Nonacarbonyldiiron-, pentacarbonyliron-, or hexacarbonylmolybdenum-induced reacions of 4,5-polymethylene-substituted 2-isoxazolines.
- Metal carbonyl-induced N-O bond cleavage of the oxime group.
- Hexacarbonylmolybdenum-induced reaction of isoxazoles. Cycloaddition of isoxazoles with acetylenic esters and related reactions.
- Deoximation of oxime O-acetates, oximes, and oxime ethers by nonacarbonyldiiron or pentacarbonyliron. An electronic effect for the N-O bond cleavage.
- Synthesis and properties of the (n)(2,5)pyridinophane ring system.
- The reaction of (Z)-2-(3-oxo-1-propenyl)-2H-azirine derivative with molybdenum carbonyl complexes.
- On the reaction of N-vinyliminophosphoranes. Part 10. On the reaction of N-vinyliminophosphoranes with 2,4,6-cyclooctatrienone. Intermediate formation of 8-azabicyclo[5.3.1]undeca-2,4,7,9-tetraene ring system.
- The reaction of N-(vinylimino)phosphoranes. Part 13. On the reaction of N-(3-oxo-2-cyclohexenyl)imino)triphenylphosphorane with .ALPHA.-bromo ketones and .ALPHA.,.BETA.-unsaturated ketones.
- Nonacarbonyldiiron-induced reaction of 3-azido-1,2,3-triphenyl-cyclopropene and 4,5,6-triphenyl-1,2,3-triazine.
- A novel formation of phenyl-substituted pyridines by the reaction of N-(diphenylphosphinyl)-1-azaallyl anions with .ALPHA.,.BETA.-unsaturated carbonyl compounds. A new synthetic equivalent of primary vinylamines.