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Methyl 2-diphenyl-phosphor-yloxy-2-aza-bicyclo-[2.2.1]hept-5-ene-3-exo-carboxyl-ate.

ABSTRACT: In the title compound, C(20)H(20)NO(4)P, the dihedral angle between the phenyl rings is 68.52 (7)°. In the crystal structure, the mol-ecules are linked by a weak C-H⋯π(arene) inter-action along [010] involving the phenyl CH group and the phenyl rings. There are no further significant inter-molecular inter-actions.

SUBMITTER: Sousa CA

PROVIDER: S-EPMC2968096 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Bicyclo-[2.2.1]hept-7-yl p-bromo-benzoate.

Project description:The title compound, C(14)H(15)BrO(2), contains a sterically unencumbered norbornyl group. The dihedral angle between the plane of the carboxyl-ate group and the mean plane of the adjacent benzene ring is 5.3?(2)°. The dihedral angle between the plane of the carboxyl-ate group and the norbornyl methano C-O bond is 4.5?(1)°, the methano C atom deviating by 0.141?(2)?Å from this plane. In the crystal, mol-ecules pack as pairs of enanti-omers, with a distance of 3.747?(1)?Å between the centroids of nearest parallel benzene rings.

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Project description:The acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicylic alkene using alcohol nucleophiles were investigated. Although this acid-catalyzed ring-opening reaction did not cleave the cyclopropane unit as planned, this represent the first examples of ring-openings of cyclopropanated 3-aza-2-oxabicyclo[2.2.1]alkenes that lead to the cleavage of the C-O bond instead of the N-O bond. Different acid catalysts were tested and it was found that pyridinium toluenesulfonate in methanol gave the best yields in the ring-opening reactions. The scope of the reaction was successfully expanded to include primary, secondary, and tertiary alcohol nucleophiles. Through X-ray crystallography, the stereochemistry of the product was determined which confirmed an SN2-like mechanism to form the ring-opened product.

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Project description:The crystal structure of the title compound, C(14)H(14)N(2), displays inter-molecular N-H?N hydrogen bonds, forming dimers of enanti-omeric mol-ecules via a crystallographic centre of inversion.

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Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Project description:Indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems with alcohols and water were investigated. Reactions of [2.2.1] bicyclic systems gave anti-1,2-, anti-1,4- and syn-1,4-ring-opened products with moderate to excellent regio- and stereoselectivity. When [2.2.2] bicyclic systems were subjected to similar reaction conditions, only anti-1,2 and anti-1,4-ring-opened products were obtained.

| S-EPMC2759854 | biostudies-literature

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Project description:In the title indoline compound, C(19)H(14)N(2)O(3)S, the pyrrolidine ring adopts an envelope conformation with the four-connected (spiro) C atom as the flap [displacement = 0.148 (3) Å]. The mean plane formed through the indoline unit is inclined at dihedral angles of 89.92 (16) and 59.54 (12)° with the thia-zole and phenyl rings, respectively; the dihedral angle between the latter rings is 9.55 (14)°. In the crystal, pairs of inter-molecular C-H⋯O hydrogen bonds link neighbouring mol-ecules into inversion dimers, producing R(2) (2)(6) hydrogen-bond ring motifs. Weak inter-molecular C-H⋯π as well as π-π inter-actions [centroid-centroid distance = 3.4041 (15) Å] further consolidate the crystal structure.

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| S-EPMC5588587 | biostudies-literature

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