0000000000412126

AUTHOR

Bernd F. Straub

0000-0001-6642-0444

showing 8 related works from this author

1,3-Benzyl Migration in Iminium Ions: Evidence for a Fast Free-Radical Chain Reaction

2011

The “exocyclic” 1,3-benzyl shift observed in iminium salts derived from 1-benzyl-1,2,3,4-tetrahydroisoquinolines is related to the “endocyclic” Knabe rearrangement. A crossover experiment, isotopic labelling, the study of initiators and inhibitors as well as DFT calculations of gas-phase model structures provide evidence for a free-radical pathway under kinetic entropy control that is not affected by “slow” radical traps.

Crossover experimentChemistryLabellingOrganic ChemistryIminiumPhysical and Theoretical ChemistryPhotochemistryChain reactionIonEuropean Journal of Organic Chemistry
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ChemInform Abstract: Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of …

2013

Remarkably, isobenzofuran and benzopyran derivatives are obtained by the title reaction and not as described in earlier publications five- or six-membered lactams.

chemistry.chemical_compoundIsobenzofuranchemistryHalogenationGeneral MedicineMedicinal chemistryBenzopyranChemInform
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Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams

2012

The iodocyclization of o-alkynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in the literature need to be revised.

Steric effectschemistry.chemical_compoundchemistryIsobenzofuranNucleophileStereochemistryAmideYield (chemistry)Organic ChemistryElectrophileTriple bondThe Journal of Organic Chemistry
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CCDC 897109: Experimental Crystal Structure Determination

2013

Related Article: Claudine Schlemmer , Lars Andernach , Dieter Schollmeyer, Bernd F. Straub , and Till Opatz|2012|J.Org.Chem.|77|10118|doi:10.1021/jo3017378

Space GroupCrystallographyN-(3-(Iodo(phenyl)methylene)-2-benzofuran-1(3H)-ylidene)methanamineCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 898755: Experimental Crystal Structure Determination

2013

Related Article: Claudine Schlemmer , Lars Andernach , Dieter Schollmeyer, Bernd F. Straub , and Till Opatz|2012|J.Org.Chem.|77|10118|doi:10.1021/jo3017378

Space GroupCrystallographyCrystal SystemN-(4-Iodo-3-phenyl-1H-isochromen-1-ylidene)anilineCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 897110: Experimental Crystal Structure Determination

2013

Related Article: Claudine Schlemmer , Lars Andernach , Dieter Schollmeyer, Bernd F. Straub , and Till Opatz|2012|J.Org.Chem.|77|10118|doi:10.1021/jo3017378

Space GroupCrystallographyCrystal SystemN-(4-Iodo-3-phenyl-1H-isochromen-1-ylidene)methanaminium triiodideCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 897106: Experimental Crystal Structure Determination

2013

Related Article: Claudine Schlemmer , Lars Andernach , Dieter Schollmeyer, Bernd F. Straub , and Till Opatz|2012|J.Org.Chem.|77|10118|doi:10.1021/jo3017378

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates2-(Acetoxymethyl)-6-((3-(iodo(345-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)methylene)-6-nitro-2-benzofuran-1(3H)-ylidene)amino)tetrahydro-2H-pyran-345-triyl triacetate pentane solvate
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CCDC 897107: Experimental Crystal Structure Determination

2013

Related Article: Claudine Schlemmer , Lars Andernach , Dieter Schollmeyer, Bernd F. Straub , and Till Opatz|2012|J.Org.Chem.|77|10118|doi:10.1021/jo3017378

Space GroupCrystallographyN-(3-(Iodo(phenyl)methylene)-2-benzofuran-1(3H)-ylidene)anilineCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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