Cyclobutane Compounds. III.<sup>1,2</sup> The Ionic Addition of Hydrogen Chloride, Hydrogen Bromide, and Hydrogen Iodide to Allene and Methylacetylene

Griesbaum, Karl; Naegele, W.; Wanless, G. G.

doi:10.1021/ja01092a026

Cited by 65 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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“…The process usually takes place according to the Markovnikoff rule and often cannot be stopped at the monoaddition stage [28]. For simple allenes, including the parent hydrocarbon, another side reaction leads to cyclodimerisation products (1,3-dihalo-cyclobutanes) [29]. With hydrochloric and hydrobromic acid, vinylallene (penta-1,2,4-triene) provides ( E )- and ( Z )-2-halo-1,3-pentadiene [21,30].…”

Section: Resultsmentioning

confidence: 99%

Polar reactions of acyclic conjugated bisallenes

Stamm¹,

Hopf²

2013

Beilstein J. Org. Chem.

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SummaryThe chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br2 and I2 addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.

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“…The authors appreciate the opportunity to show that the theoretical calculations reported in Barnett and Capitani's paper are consistent with our results obtained experimentally by the study of the dipole moments of 1,3-dihalocyclobutanes. 15. trans-1,3-dibromo-1,3-dimethylcyclobutane was prepared by the method of Griesbaum et al [12] by the reaction of allene with hydrogen bromide at dry-ice temperature. Hydrogen bromide was bubbled into the liquefied allene.…”

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confidence: 99%

Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

Lampman

Aumiller

2005

Int J of Quantum Chemistry

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ABSTRACT:The dipole moments of cis and trans-1,3-dichloro-, 1,3-dibromo-, and 1,3-diiodocyclobutanes were obtained. The deviation from planarity (angle of puckering) was calculated from the dipole moments. In all cases, the compounds were found to be non-planar (puckered). Although the angle strain increases slightly for a non-planar ring, the decrease in torsional strain becomes more important. For the cisseries, it was found that the angle of puckering was largest for the 1,3-diiodocyclobutane. For the trans-series the angle of puckering was the least for the 1,3-diiodocyclobutane. trans-1,3-Dibromo-1,3-dimethylcyclobutane has the least amount of puckering of all the compounds studied.

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Cyclobutane Compounds. III.^1,2 The Ionic Addition of Hydrogen Chloride, Hydrogen Bromide, and Hydrogen Iodide to Allene and Methylacetylene

Cited by 65 publications

References 0 publications

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

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

Polar reactions of acyclic conjugated bisallenes

Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

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Cyclobutane Compounds. III.1,2 The Ionic Addition of Hydrogen Chloride, Hydrogen Bromide, and Hydrogen Iodide to Allene and Methylacetylene

Cited by 65 publications

References 0 publications

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

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

Polar reactions of acyclic conjugated bisallenes

Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

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Cyclobutane Compounds. III.^1,2 The Ionic Addition of Hydrogen Chloride, Hydrogen Bromide, and Hydrogen Iodide to Allene and Methylacetylene