Dichotomies in microwave-assisted propargyl-isomerization-Claisen domino sequences dependent on base strengths.
Microwave-assisted unimolecular isomerization-Claisen domino reactions of 1,3-di(hetero)aryl propargyl trityl ethers lead, depending on the basicity of the amine, either to the formation of tricyclo[3.2.1.0(2,7)]oct-3-enes (with triethylamine) or to indanes (with DBU). Based upon product analyses and computations, this base dependent dichotomy can be rationalized as a sequel of pericyclic reactions with intermediate protonation and deprotonation.
D'Souza
Daniel M
DM
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69121 Heidelberg, Germany.
Liao
Wei-Wei
WW
Rominger
Frank
F
Müller
Thomas J J
TJ