Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas

Resum

The 1,3-dipolar cycloaddition was launched in the early 1960s as general synthetic procedure yielding five-membered rings. The protocols have been considerably boosted and currently constitute a versatile toolbox leading to a variety of heterocyclic systems. In this context, this PhD thesis is aimed at synthesizing a series of rigid mesoionic heterocycles, thioisomünchnone derivatives in particular. Such compounds behave as 1,3-dipoles against dipolarophiles giving rise to heteroatom-rich systems, which are otherwise difficult to obtain by means of alternative strategies. Moreover, a comprehensive theoretical analysis has been performed in conjunction with the experimental work, in order to rationalize the stereoelectronic effects controlling the 1,3-dipolar cycloaddition.