Synthesis of Bis(1,2-fused tricyclic cyclopropenes)

• Main Authors: Tsai, Ming-Chia, 蔡明佳
• Other Authors: Lee, Gon-Ann
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/22910218597898425800

碩士 === 輔仁大學 === 化學系 === 101 === 1-Bromo-2,2-dichloro-1-trimethylsilylcyclopropane (5) reacted with 1.8 equiv. tetra-n-butylammonium fluoride and cyclopentadiene to give 2-Bromo-4-chlorotricyclo[3.2.1.02,4]oct-6-ene (7). The key precursor 53 for the synthesis of bis(1,2-fused tricyclic cyclopropene) 52 was arised from compound 7 reacted with diiron nonacarbonyl. Compound 54 protected with ethylene glycol to afford compound 53 in acidic condition. Compound 53 was treated with 2.2 equiv. methyllithiun followed by reacting with diphenylisobenzofuran (DPIBF) to give exo-exo adduct 59 and exo-exo, exo-exo adduct 60. By the way, the reaction mixture was heated in acdic condition to from aromatic product 66. In other hand, treatment of 53 with 9 equiv. methyllithium folloed by reacting with DPIBF to give 60、endo-exo, endo-exo adduct 50 and exo-exo, endo-exo adduct 62.