Heterotricyclodecane X. 2-Oxa-7-thia-isotwistan und 2-Oxa-7-thia-twistan sowie Derivate

The synthesis of 2-oxa-7-thia-isotwistane ( 11 ) and 2-oxa-7-thia-twistane ( 22 ) as well as of several of their derivatives is described starting from endo-2-hydroxy-9-thiabi cyclo[3.3.1]non-6-ene ( 4 ). The 10^O(2)-isotwistane bromide 13 , iodide 14 and tosylate 30 as well as the 10^S(7)-isotwistane iodide 15 , tosylate 20 , and the 10^S(7)-twistane tosylate 21 were treated under reaction conditions suitable for molecular rearrangements involving the epi-sulfonium ion i and the oxonium ion g . respectively, by neighbouring group participation.