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N ‐Nitrosodecahydroquinolines 3 ‐Nitrogen‐15 Nuclear Magnetic Resonance Spectra
Author(s) -
Vierhapper Friedrich W.,
Srinivasan Puliyur R.
Publication year - 1982
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270190312
Subject(s) - chemistry , nitroso , planarity testing , ring (chemistry) , nitrogen , nitrosation , nitroso compounds , stereochemistry , medicinal chemistry , crystallography , organic chemistry
15 N Chemical shifts of N ‐nitroso‐ trans ‐decahydroquinoline, N ‐nitroso‐ cis ‐decahydroquinoline, of 12 methyl‐or t ‐butyl‐substituted N ‐nitrosodecahydroquinolines and of N ‐nitroso‐ trans‐syn‐trans ‐perhydroacridine are reported. Shift effects for N ‐nitrosation were calculated by comparison with the parent amines. Shift effects for ring substitution, obtained by comparison with the data of N ‐nitrosopiperidine, are of similar direction and magnitude as in the parent amines for the ring nitrogens (N‐1). Methyl substitution nearly always causes deshielding for the nitroso nitrogens (N‐2), with a very large deshielding if the planarity of the (C‐α) 2 NNO region is disturbed.