Synthesis of 9-Methoxymethyl-18-methyl-2,11-dithia[3.3]metacyclophane: a Dithia[3.3]metacyclophane With a Protected Internal Benzylic Functional Group

Abstract

A synthetic route to a dithia [3.3] metacyclophane with a benzylic functional ( methoxymethyl ) group at C9 is described. The benzylic function however had to be introduced at a later stage in the synthetic scheme to optimize the overall yield. Only the anti isomer of the desired dithiacyclophane (7) was isolated. The entire methoxymethyl group lies within the shielding zone of the opposite benzene ring as indicated in the ¹H n.m.r. spectrum. Attempts to convert anti-(7) into the novel aromatic system (5b) by a rearrangement-elimination sequence however failed.