Allenyl Cations Research Articles

Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides

Conjugated arylacetylenic ketones and aldehydes, propargyl-type alcohols, and arylacetylenes reacted with arenes in the presence of AlBr3 or AlCl3 as catalyst to give substituted indenes. 3-Arylpropynoic acids under analogous conditions gave rise to 3,3-diarylindan-1-ones, while the corresponding methyl esters were converted into methyl 3,3-diarylprop-2-enoates. The key intermediates in the transformations of acetylenic ketones and aldehydes and propargyl-type alcohols into indene derivatives are resonance-stabilized propargyl—allenyl cations -C≡ C-C+ ↔ -C+=C=C which reacted with one of the resonance structures to give isomeric indenes, depending on the substituent nature.

Intramolecular Catalytic Friedel—Crafts Reactions with Allenyl Cations for the Synthesis of Quinolines and Their Analogues.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues.

[reaction: see text] This paper describes a novel method to synthesize a quinoline backbone by incorporating allenyl cations into a catalytic intramolecular Friedel-Crafts reaction. The initial products were isomerized and aromatized upon treatment with acid and base, respectively, to give quinolines. The basic concept also proved to be promising for 1-benzazepine, 1-benzazocine, or isoquinoline synthesis.

Spectroscopic Characterization, Reactivity, and Reactions of (Arene)Cr(CO)3-Stabilized γ-Propargyl−Allenyl Cations

(Arene)Cr(CO)3-stabilized γ-propargyl−allenyl cations Cr(CO)3(η6-R1C6H4)C⋮CC+R2R3 (2) are reactive intermediates in the synthesis of arene-complex-substituted allenes or propargyl derivatives using...

A reaction of γ-chalcogen-substituted prop-2-ynyl cations with mild nucleophiles

γ-Chalcogen-substituted prop-2-ynyl cations are generated by the reactions of diethyl acetals 1 and 2 with BF3–Et2O and react with various mild nucleophiles without isomerisation to allenyl cations to afford the prop-2-ynylated products 3a–e and 5a–c in good yields.

Synthesis of cyclopentenes via [3 + 2]-cycloadditions of silylated propargyl .tautm. allenyl cations with alkenes

Synthesis of cyclopentenes via [3 + 2]-cycloadditions of silylated propargyl .tautm. allenyl cations with alkenes

ChemInform Abstract: Formation of Allenyl Cations by Photolysis of Triarylchloroallenes.

AbstractDie Photolyse von Triarylallenen (I) in Gegenwart von Alkoholen (II) zu den Photolyseprodukten (III)‐(V) wird beschrieben.

ChemInform Abstract: ADDITION AND CYCLOADDITION REACTIONS OF ALLENYL CATIONS WITH ACYCLIC 1,3‐DIENES

Chemischer InformationsdienstVolume 14, Issue 4 Preparative Organic Chemistry ChemInform Abstract: ADDITION AND CYCLOADDITION REACTIONS OF ALLENYL CATIONS WITH ACYCLIC 1,3-DIENES H. MAYR, H. MAYRSearch for more papers by this authorH. KLEIN, H. KLEINSearch for more papers by this author H. MAYR, H. MAYRSearch for more papers by this authorH. KLEIN, H. KLEINSearch for more papers by this author First published: January 25, 1983 https://doi.org/10.1002/chin.198304102Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume14, Issue4January 25, 1983 RelatedInformation

ChemInform Abstract: AB INITIO MO STUDY OF METHYL AND PHENYL‐SUBSTITUTED ALLENYL CATIONS

Chemischer InformationsdienstVolume 14, Issue 4 Physical Organic Chemistry ChemInform Abstract: AB INITIO MO STUDY OF METHYL AND PHENYL-SUBSTITUTED ALLENYL CATIONS H. MAYR, H. MAYRSearch for more papers by this authorR. SCHNEIDER, R. SCHNEIDERSearch for more papers by this author H. MAYR, H. MAYRSearch for more papers by this authorR. SCHNEIDER, R. SCHNEIDERSearch for more papers by this author First published: January 25, 1983 https://doi.org/10.1002/chin.198304059Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume14, Issue4January 25, 1983 RelatedInformation

Stepwise [2 + 2] and [3 + 2] "cycloaddition" reactions of allenyl cations with olefins

Stepwise [2 + 2] and [3 + 2] "cycloaddition" reactions of allenyl cations with olefins

Addition and cycloaddition reactions of allenyl cations with various cycloalka-1,3-dienes

Allenyl cations ▪, generated in situ from propargyl chlorides and zinc chloride give monocyclic adducts or [3+4] and [2+4] cycloaddition products with various cycloalka-1,3-dienes. The mode of addition depends on R and the ring size of the 1,3-dienes.

Competing [3+4]‐ and [2+4]‐Cycloadditions of Allenyl Cations

A facile synthesis of bicyclo[3.2.1]octa-2,6-dienes (3), R1 = alkyl, and 5-(aryl-methylene)norbornenes (4), R1 = aryl, is possible by cycloaddition of allenyl cations (2) to cyclopentadiene. (2) was generated from propargyl halides (1) with catalytic amounts of ZnCl2 in ether/CH2Cl2.

Orientation effects in reactions of allenyl cations with styrene

Allenyl cations, generated in situ from allenyl or alkynyl halides and Ag +, attack styrene at the side chain or at the aromatic nucleus. The allenyl/alkynyl product ratio is dependent on the structure of the precursor halide except for highly substituted systems.

Orientation effects in reactions of allenyl cations with styrene

Orientation effects in reactions of allenyl cations with styrene

4 + 3]‐Cycloadditions of Allenyl Cations

4 + 3]‐Cycloadditions of Allenyl Cations