866412-83-1Relevant academic research and scientific papers
Intermolecular tandem addition-cyclization of bromoallenes: A facile synthesis of methylenecyclopropyl carboxylates and polysubstituted furans
Xu, Lubin,Huang, Xian,Zhong, Fangrui
, p. 5061 - 5064 (2006)
(Chemical Equation Presented) The base-mediated reactions of 1,3-dicarbonyl compounds with bromoallenes used as an allyl dication equivalent were explored. The corresponding dimethyl methylenecyclopropane-1,1-dicarboxylates and 2,3,4-trisubstituted furans
An efficient stereoselective synthesis of 4,5-trans-1,5-cis-3-oxabicyclo[3. 1.0]hexan-2-ones via the iodolactonization of alkylidenecyclopropyl esters
Ma, Shengming,Lu, Lianghua
, p. 7629 - 7633 (2005)
A highly stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH3CN to afford 4,5-trans-1,5-cis-3-oxabicyclo-[3.1.0]hexane-2-ones is described. The reaction is very general, accommodating a wide range of substituents. A plausible mechanism that explains the essential role of water in this reaction is proposed.
Catalytic, formal homo-Nazarov-type cyclizations of alkylidene cyclopropane-1,1-ketoesters: Access to functionalized arenes and heteroaromatics
Aponte-Guzman, Joel,Taylor, J. Evans,Tillman, Elayna,France, Stefan
supporting information, p. 3788 - 3791 (2014/08/05)
A catalytic, formal homo-Nazarov-type cyclization of alkylidene cyclopropanes (ACPs) to give functionalized arenes and heteroaromatics is reported. In the presence of a Lewis acid catalyst, the ACP 1,1-ketoesters undergo distal bond cleavage to afford an allyl cation intermediate. Adjacent π-attack on the allyl cation then provides a six-membered ring that undergoes rapid aromatization. In these cases, benzenoid products are formed in up to 98% yield. Strategic choice of the substitution about the ACP allows for the generation of other useful isomeric products in good yields.
DBU-mediated transformation of arylmethylenecyclopropenes to alkylidenecyclopropanes
Sang, Rui,Yang, Hai-Bin,Shi, Min
, p. 3591 - 3594 (2013/07/05)
An interesting DBU-mediated intramolecular isomerization of arylmethylenecyclopropenes 1 to alkylidenecyclopropanes (ACPs) has been described in this context. A variety of ACPs were obtained through a base-assisted manner in moderate to good yields under mild conditions with good stereoselectivities in most cases.
