Premium
Medium‐sized heterocycles: Synthesis of a 2,10‐Bis(alkoxycarbonyl)‐substituted 6‐Oxo‐12 H ‐dibenzo[ d,g ][1,3,2]dioxaphosphocin
Author(s) -
Pastor Stephen D.,
Spivack John D.
Publication year - 1991
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.5570280617
Subject(s) - geminal , chemistry , cyclohexane conformation , methylene , coupling constant , stereochemistry , proton , medicinal chemistry , crystallography , organic chemistry , molecule , hydrogen bond , physics , particle physics , quantum mechanics
The synthesis and characterization of a 2,10‐bis(alkoxycarbonyl)‐substituted 6‐oxo‐12 H ‐dibenzo[ d,g ][1,3,2]‐dioxaphosphocin, 6 , is described. The lack of an observable 5 J HP coupling of phosphorus to the downfield C‐12 methylene proton and the observation of a 2 J HCH geminal coupling constant of 14 Hz suggest that the conformation of 6 in solution is not solely a boat‐chair conformation, but may involve a rapid equilibrium of the boat‐chair with either a boat or twist‐boat conformation.