Dimerization of planarized diamine 2 using benzoyl peroxide gave dihydrazine 1 in about 70% yield; that is, three dehydrogenations (one CC- and two NN-homocouplings) and two ring closures were attained in one synthetic step. Dihydrazine 1 may be viewed as a chiral π-conjugated conjoined double helicene, with two homochiral helicene-like fragments, annelated in their mid-sections. A relatively high barrier of ∼35 kcal mol-1 for inversion of configuration for one of the helicene-like helices in 1 was found.
ASJC Scopus subject areas
- Colloid and Surface Chemistry