The concept of homoaromaticity has its origins in the debate over the non-classical carbonium ions that occurred in the 1950s. Saul Winstein, a famous proponent of the non-classical ion model, first described homoaromaticity while studying the 3-bicyclo[3.1.0]hexyl cation.
In a series of acetolysis experiments, Winstein et al. observed that the solvolysis reaction occurred empirically faster when the tosyl leaving group was in the equatorial position. The group ascribed this difference in reaction rates to the anchimeric assistance invoked by the "cis" isomer. This result thus supported a non-classical structure for the cation.
Winstein subsequently observed that this non-classical model of the 3-bicyclo[3.1.0]hexyl cation is analogous to the previously well-studied aromatic cyclopropenyl cation. Like the cyclopropenyl cation, positive charge is delocalized over three equivalent carbons containing two π electrons. This electronic configuration thus satisfies Huckel's rule (requiring 4n+2 π electrons) for aromaticity. Indeed, Winstein noticed that the only fundamental difference between this aromatic propenyl cation and his non-classical hexyl cation was the fact that, in the latter ion, conjugation is interrupted by three -- units. The group thus proposed the name "tris-homocyclopropenyl"—the tris-homo counterpart to the cyclopropenyl cation.