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Syntheses and conformations of some cyclic hydroxamates. X‐Ray crystal structure of 2‐( p ‐nitrobenzoyl)tetrahydro‐2 H ‐1,2‐oxazine
Author(s) -
Johnson James Elver,
Hodzi Richard,
Todd Susan L.,
De Meester Patrice,
Chu Shirley S. C.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230534
Subject(s) - chemistry , monoclinic crystal system , alkylation , crystal structure , potassium , crystallography , oxygen atom , crystal (programming language) , x ray , nmr spectra database , stereochemistry , spectral line , molecule , organic chemistry , catalysis , physics , quantum mechanics , computer science , programming language , astronomy
Alkylation of potassium p ‐nitrobenzohydroxamate with 1,4‐dibromobutane gave 2‐( p ‐nitrobenzoyl)tetrahydro‐2 H ‐1,2‐oxazine (3). The X‐ray crystal structure of 3 has been determined. The crystals are monoclinic, space group P2 1 /n with a = 6.749(1), b = 7.644(1), c = 21.557(2)Å, β = 98.89(1), V = 1098.8(2)Å 3 and Z = 4. The structure, which was refined to R = 0.039 using 1340 observed reflections, shows the oxazine and carbonyl oxygen atoms trans to each other. Alkylation of potassium benzohydroxamate with 1,3‐dibromobutane gave a mixture of 3‐methyl‐2‐benzoyloxazolidine (4) and 5‐methyl‐2‐benzoyloxazolidine (5). The 1 H and 13 C nmr spectra of the mixture of 4 and 5 indicates that these cyclic hydroxamates exist predominantly in the s‐trans conformation.