5-Allyl-9-oxobenzomorphans. Part 2. The crystal and molecular structure of an unusual product of dequaternization of 5-Allyl-9-oxobenzomorphan methobromide.

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DOIResolve DOI: http://doi.org/10.1139/v75-467
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume53
Issue21
Pages32763284; # of pages: 9
AbstractThe synthesis of 5-allyl-2'-methoxy-9-oxo-6,7-benzomorphan (5b) is described. The 10-hydroxy-2-methyl-1,11-propano-9H-indeno-1,2,10,11-tetrahydro[2,1-c]pyridine (7a) and the corresponding 6-methoxy derivative (7b) are unexpected products of pyrolysis of 5-allyl-2-methyl-9-oxobenzomorphan methobromide (4a) and 5-allyl-2′-methoxy-2-methyl-9-oxobenzomorphan methobromide (4b) respectively. The molecular structure of 7a (C16H19NO) has been determined from spectral and microanalytical data, and confirmed by X-ray single crystal analysis on its hydrobromide salt using the heavy atom technique. The crystals of [C16H20NO]+Br− are monoclinic, P21/a, with a = 13.724(2), b = 14.022(3), c = 7.495(2) Å, β = 97.33(5)°, and Z = 4. The crystal structure has been refined by block-diagonal least-squares calculations to R and Rw = 0.036 for the 2197 observed reflections. The N atom has planar trigonal coordination, and forms one double and two single C—N bonds of lengths 1.273(4), 1.465(4), and 1.474(4) Å, respectively. The Br is hydrogen-bonded to O. The N and O atoms are trans.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada
Peer reviewedYes
NRC number14833
NPARC number21274984
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Record identifiereb0554b5-45d9-473b-8020-550004c9aa0e
Record created2015-05-04
Record modified2016-05-09
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