EN ROUTE TO TETRA-t-BUTYLETHYLENE

Article abstract of DOI:10.1016/S0040-4020(01)87586-4

Triene 22 was synthesized and converted by two different routes to the tetraaldehyde 27, the first "non-bridged" derivative of 1.An X-ray analysis of 27 reveals that the C=C bond is twisted by 28.6 deg.Attempts to prepare 1 from 27 failed, thus far.Addition of t-buthyllithium to 13, subsequent reaction with ethylene oxide and further reactions led to the highly strained tri-t-butylethylethylene 33; according to force field calculations 33 has the largest fragmentation strain of all synthesized hydrocarbons of this type.