Compounds with bridgehead nitrogen. Part 47. The reaction between trans-1-aminobenzocycloalkan-2-ols and formaldehyde

Abstract

The reaction between trans-1-aminoindan-2-ol and formaldehyde and between trans-1-amino-1,2,3,4-tetrahydronaphthalen-2-ol and formaldehyde yields 5,r-5a,t-8a,13,c-13a,t-16a-hexahydro-8,16-methanodi-indeno[1,2-d : 1′,2′-i][1,6,3,8]dioxadiazecine and 5,6,r-6a,c-9a,14,15,t-15a,t-18a-octahydro-9,18-methanodinaphtho[1,2-d : 1′,2′-i][1,6,3,8]dioxadiazecine respectively whereas the reaction between trans-1-amino-2-hydroxy-6,7,8,9-tetrahydro-5H-benzocycloheptane and formaldehyde yields bis(1,3a,4,5,6,10b-hexahydro-2H-benzo[6,7]cyclohept[1,2-d]oxazol-1-yl)methanes.