Compounds with Bridgehead Nitrogen

Article abstract of DOI:10.1002/mrc.1260241209

In contrast to the reported reaction between trans-1-aminotetralin-2-ol and formaldehyde, which gives r-6a,c-9a,t-15a,t-18a-5,6,6a,9a,14,15,15a,18a-octahydro-9,18-methanodinaphtho<1,2-d:1',2'-i><1,6,3,8>dioxadiazecine, an examination of the δ 4.0-5.0 region of the 1H NMR spectra of the products of the reaction between trans-3-aminotetralin-2-ol and formaldehyde showed these to be a 50:50 mixture of r-5a,t-8a,c-14a,t-17a- and r-5a,c-8a,t-14a,t-17a-5,5a,8a,9,14,14a,17a,18-octahydro-8,17-methanodinaphtho<2,3-d:2',3'-i><1,6,3,8>dioxadiazecine.In a similar way, the reaction between trans-2-aminocyclohexanol and formaldehyde was reexamined and found to produce initially a ca 80:20 mixture of r-4a,t-7a,c-11a,t-14a- and r-4a,c-7a,t-11a,t-14a-7,14-methanoperhydrodibenzo<1,6,3,8>dioxadiazecines. KEY WORDS Octahydro-8,17-methanodinaphtho<2,3-d:2',3'-i><1,6,3,8>dioxadiazecine 7,14-Methanoperhydrodibenze>1,6,3,8>dioxadiazecines 1H NMR Geminal coupling constants trans-3-Aminotetralin-2-ol