The Addition of Hydrogen Chloride to Aliphatic Allenic Hydrocarbons<sup>1</sup>

Jacobs, Thomas L.; Johnson, Robert N.

doi:10.1021/ja01509a050

Cited by 53 publications

(19 citation statements)

References 2 publications

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“…It is known that interaction of 1,1‐dimethyl and tetramethyl‐substituted allenes with electrophilic agents results into a stable carbonium cations which are capable to eliminate proton from methyl group to give 1,3‐diene system . To develop a general method for the synthesis of 8‐ylidene decorated benzazecines we applied the described electrophile‐triggered dehydrogenation in substituents of acyclic allenes to obtain benzazecines 2aa–2fb .…”

Section: Resultsmentioning

confidence: 99%

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

et al. 2020

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We have elaborated a general and simple microwave-assisted method for the synthesis of original 8-ylidene decorated benzazecines. We have shown that under the action of electron-deficient alkynes in acetic acid the starting benzoannulated azacyclic allenes or 1-alkyl(benzyl)-1-phenylethynylsubstituted isoquinolines underwent transformations leading to benzazecines in high yields. In acetic acid all reactions pro-[a] Dr. A. A. Titov, M. S. Results and DiscussionWe initiated our study with estimating the influence of protonic solvents on the transformations of phenylethynyl decorated isoquinolines 1a-g under the action electron-deficient alkynes. The starting 1-alkyl(benzyl)-1-phenylethynyl-6,7-dimethoxyisoquinolines 1a-g were synthesized according to the previously described procedure [23] from 1-alkyl(benzyl)-3,4-dihydroisoquinolinium methiodide derived via the Bischler-Napieralski reaction followed by alkylation [20] (Scheme 1). Scheme 1. Synthesis of starting 1-alkyl(benzyl)-1-phenylethynyl-6,7-dimethoxyisoquinolines 1a-g.Scheme 3. Reactions of isoquinolines 1b-g with methyl propiolate in HFIP.

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Section: Resultsmentioning

confidence: 99%

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

et al. 2020

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“…[11,[24][25][26] Most protonation reactions are irreversible due to the formation of an allylic carbonium intermediate. At first, we investigated the reaction of tetraphenylallene with trifluoroacetic acid (TFA) in THF.…”

Section: Resultsmentioning

confidence: 99%

The First Conjugated Allene Polymer

Kijima¹,

Hiroki

Shirakawa

2002

Macromol. Rapid Commun.

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“…A classical mechanism including the intermediate formation of the episulfonium ion has been proposed for these reactions. 91,92 The addition of 2,4-dinitrobenzenesulfenyl chloride to various allenes has been studied. 93 It was shown that adducts of the type 37 containing a 2,4-dinitrophenylthio group at the double bond are the main reduction products; regioisomeric compounds of the type 38 were formed in smaller amounts and with only some of the substrates studied.…”

Section: Electrophilic Sulfenylation Of Allenesmentioning

confidence: 99%