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Abstract
Two products were isolated from the iodine-induced cyclization reaction of di-n-propyl-4-pentenyl-phosphonate, 1. One of them has previously been proven to be 2-n-propyloxy-2-oxo-6-(iodomethyl)-1,2-oxaphosphorinane, 2. The second product, 3, has the same molecular weight and mass spectral fragmentation patterns as 2. The results of one- and two-dimensional 1H. 13C. and 31P multinuclear magnetic resonance spectroscopies indicate that 2 and 3 are the alkoxyl-axial and alkoxyl-equatorial diastereoisomers, respectively, of 2-n-propyloxy-2-oxo-6-(iodomethyl)-1, 2-oxaphosphorinane. The nuclear magnetic resonance spectroscopic parameters such as the 1H, l3C, and 31P chemical shifts and the homo-(1H–1H) and hetero-(1H–13C, lH 31P, and 13C – 31P)coupling constants of 2, and 3 are documented in this report.
All NMR spectra were obtained from the Biophysics NMR Facility Center, Johns Hopkins University, established by a N.I.H. grant GM-27512 and the work was also partially supported by a N.I.H. grant GM 34252 (to LSK). We wish to thank Dr. Daniel Callahan and Mr. Chang Lee for editorial assistance, and the grant from the Chinese National Science Foundation.