The unusual course of the high-pressure reaction of 1,10-diaza-[18]-crown-6 with α,ω-diiodo ethers

Simple 1,10-diaza-[18]-crown-6 reacts smoothly with di(2-indoethyl)ether under high-pressure (10 kbar) to give a bis-quaternary spiro salt as a major product, whereas the analogous reaction with 1,8-diiodo-3,6-dioxaoctane leads to the expected precursor of a [2.2.2] cryptand.