By Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao
This paintings on small ring compounds in natural synthesis covers cycloadditions onto methylene- and alkylidenecyclopropane, and selective modifications of small ring compounds in redox reactions.
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Additional info for 178 Topics in Current Chemistry: Small Ring Compounds in Organic Synthesis V
It is well known that angle strain in a dipolarophile can affect its reactivity and that this effect is not properly accounted for by P M O approach [72, 73]. It has been observed that a decrease in angle strain on going from educts to adducts induces an increase in reaction rate . Consequently, the higher reactivity of methylenecyclopropane compared with 1,1-dialkylethylenes may well simply reflect a decrease in angle strain of the cyclopropylidene system along the reaction coordinate, and there is no cogent need to look for additional effects.
Cycloadditionof 129 to activated dienophiles Entry Allylidene cyclopropanes "~ ~" TBDMSO 129 Dienophiles Reaction conditions i O2Me benzene 12 h°C 110 "CO2Me 132(70) II neat 0oc 30 min CHO 130 NC. CN CN CN 134 (56~N O O 135(39) case is probably due to the different steric hindrance of the isopropyl group compared to the methyl on the p-quinone in the endo transition state . The cycloaddition of acetoxy derivative 136b with 139 also occurred regiospecifically and gave only the endo cycloadduct 148 (entry 7) .
Moreover, alkylidenecyclopropanes exhibit a substantially unpolarized double bond in striking contrast with experimental data [67b]. 8 Kcal/mole difference in favor of the transition state leading to the 4-spirocyclopropane isoxazolidine for 2,2-dimethylmethylenecyclopropane, was unable to predict the lack of regioselectivity with MCP . To explain the regiochemical outcome of the reaction, another rationale approach could be undertaken. There is still ample debate among theoretical chemists about concertedness or unconcertedness of pericyclic reactions [76-78].
178 Topics in Current Chemistry: Small Ring Compounds in Organic Synthesis V by Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao