The synthesis of some t-butyloctahydronaphthalenes

Abstract

The unambiguous syntheses of eleven t-butyloctahydronaphthalenes are described. Those obtained in pure states are 2-t-butyl-1,2,3,4,5,6,7,8- octahydronaphthalene (1), 7α-t-butyl-1,2,3,4,4aα,5,6,7- octahydronaphthalene (2), 2α-t-butyl-1,2,3,4,4aα,5,6,7- octahydronaphthalene (4), 2α-t-butyl-1,2,3,4,-4aβ,5,6,7- octahydronaphthalene (5), 3α-t-butyl-1,2,3,4,4aβ,5,6,7- octahydronaphthalene (14), 7-t-butyl-1,2,3,4,4aβ,5,6,8aβ- octahydronaphthalene (27), 6-t-butyl-1,2,3,4,4aβ,5,8,8aβ-octahydronaph- thalene (28) and 2α-t-butyl-1,2,3,4,4aβ,5,6,8aβ-octahydronaphthalene (57). 7α-t-Butyl-1,2,3,4,4aβ,-5,6,7-octahydronaphthalene (3) was obtained in a state of 95% purity while 6α-t-butyl-1,2,3,4,4aβ,-5,6,7- octahydronaphthalene (15) and 6α-t-butyl-1,2,3,4,4aβ,5,6,8aβ-octahydronaphthalene (33) were obtained as inseparable mixtures with (14) and (28), respectively.