title: Conformational Study of Some Saturated 2-[Bis(2-chloroethyl)amino]-1,3,2-benzoxazaphosphorinane 2-Oxides.
abstract: Conformational analyses of cis- and trans-fused 2-[bis(2-chloroethyl)amino]-3,4,4a,5,6,7,8,8a-octahydro-1,3,2-benzoxazaphosphorinane 2-oxides and their 3-methyl and 3-benzyl derivatives were performed by (1)H, (13)C, (31)P, and variable-temperature NMR methods. Depending on the P-2 configuration and the substituent on N-3, different equilibria between chair-chair and chair-twist-boat conformations were found for the trans-fused isomers. The N-3 substituent shifts the equilibrium toward the chair-twist-boat to an extent varying in the sequence methyl > benzyl > hydrogen. In the cis-fused isomers, the nature of the N-3 substituent affects the equilibrium between the O-in and O-out conformations in the same sequence.
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland, and Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, POB 121, H-6701, Szeged, Hungary.
authors.forename: Tapio
authors.initials: T
authors.lastname: Viljanen
authors.forename: Petri
authors.initials: P
authors.lastname: Tähtinen
authors.forename: Kalevi
authors.initials: K
authors.lastname: Pihlaja
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp