1,2-Dihydropentalenes from fulvenes by [6 + 2] cycloadditions with 1-isopropenylpyrrolidine.
In situ generated acetone pyrrolidine enamine undergoes [6 + 2] cycloadditions with fulvenes to give 1,2-dihydropentalenes. This ring annulation method works particularly well with 6-monosubstituted fulvenes and is subject to steric hindrance at C-6 of the fulvene. On the basis of mechanistic studies, optimal conditions have been developed for a one-pot synthesis of 1,2-dihydropentalenes using catalytic amounts of pyrrolidine.
Department of Chemistry and Biochemistry, San Francisco State University, 1600 Holloway Avenue, San Francisco, California 94132, United States.
Necdet
N
Coşkun
Jingxiang
J
Ma
Saeed
S
Azimi
Christian
C
Gärtner
Ihsan
I
Erden
D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*
D003517:Cyclopentanes; D011759:Pyrrolidines; C017332:fulvene; C024646:pentalenene; C032519:pyrrolidine