Synthesis of Adamantane Derivatives. IX. The Ritter Reaction of 1-Hydroxymethyladamantane with Acetonitrile
スポンサーリンク
概要
- 論文の詳細を見る
The Ritter reactions of 1-hydroxymethyladamantane (<B>1</B>) and 3-homoadamantanol (<B>14</B>) with acetonitrile in coned, sulfuric acid were investigated. Two products, <I>N</I>-3-homoadamantyl acetamide (<B>2</B>) and <I>N</I>-1-adamantylmethyl acetamide (<B>3</B>) were isolated. Their total- and relative yields were determined in various reaction conditions by GLG analysis, indicating the facile conversion of <I>N</I>-3-homoadamantyl acetonitrilium cation (<B>12</B>) into <I>N</I>-1-adamantylmethyl acetonitrilium cation (<B>13</B>).
著者
-
Eguchi Shoji
Institute Of Applied Organic Chemistry Faculty Of Engineering Nagoya University
-
Toru Takeshi
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
-
Toru Takeshi
Institute for Biomedical Research, Teijin Ltd.
-
Sasaki Tadashi
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
-
Ito Katsumi
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
関連論文
- New Method for Derivatization of Squaric Acid to Highly Substituted Cyclobutenones : Lewis Acid-Catalyzed Reaction of Cyclobutene-1,2-dione Monoacetal and Its Vinylog with Unsaturated Organosilanes, and Subsequent Ring Transformation of the Adducts
- BF_3-Catalyzed Reaction of Cyclobutene-1,2-dione Monoacetal and Its Vinylog with Allylsilanes. Regioselective Synthesis of 4-Allyl-4-ethoxycyclobutenones from Squaric Acid and Their Conversion to Bi-and Tricycloalkanones
- Buckminesterfullerene C_ -ο-Quinone Methide Cycloadduct
- Radical cyclization to seleno-substituted thiahomoprotoadamantanone and its unexpected conversion to the vinyl selenide.
- Synthesis of Adamantane Derivatives. IX. The Ritter Reaction of 1-Hydroxymethyladamantane with Acetonitrile
- Crystal structure of an 8,5'-iminocarbonyloxy-bridged guanine nucleoside methanol solvate.
- Syntheses of Fused Heterocycles via Cycloaddition of Hetaryne. Studies on Heteroaromaticity. Part XLVII
- The preparation of 3,5-diacetoxy-1-cyclopentene.
- Michael Cycloaddition of 2-Phenylethene-1-sulfonamide with Carbon Disulfide
- Formation of Trithiocarbonate by the Reaction of 2,2-Diphenylethylenesulfonamide and Carbon Disulfide
- Studies on Reactions of Isoprenoids. VIII. Reactions of Sulfur Dichloride with Certain Cyclic-Acyclic 1,5-Dienes
- Studies on Heteroaromaticity. XXXVII. 1,3-Dipolar Cycloaddition of a Nitrilimine Possessing a Nitrofuran Ring
- Smiles-Type Rearrangement of N-trans-Styrylsulfonyl) and N-(4-Phenyl-1,3-butadienylsulfonyl)thioureas and Isothioureas
- Synthesis of Arylethylenesulfonamides and Intramolecular Rearrangement of N-(Arylethylenesulfonyl)thioureas
- Studies on Heteroaromaticity. XLIV. Reactivities of Benzoyl Cyanide N-Oxide and Some Derivatives Therefrom
- Reactions of Aromatic Hydroxamoyl Chlorides with Benzamidoxime Involving a Novel Synthesis of the 1,4-Dioxa-2,5-diazine Ring System
- Studies on Reactions of Isoprenoids. XI. Stereochemistry of the Ritter Reaction Products of Camphene with Unsaturated Nitriles
- The Reaction of Iodine Azide with Diphenylfulvene
- Chemistry of Cyanoacetylenes. Part XIV. One-step Synthesis of Some Ethynyl Heterocycles and Their Reactions with Diazomethane