The Synthesis and Chemistry of 1,3-Fused Tricyclic Cyclopropenes
碩士 === 輔仁大學 === 化學系 === 98 === 1-Bromo-2,2-dichloro-3-trimethylsilylcyclopropane (54) was the key precursor to synthesize the 1,3-fused tricyclic cyclopropanes. Cyclopropane 54 was treated with 1.5 equiv. methyllithium followed by reacting with cyclopentadiene to give 2-chloro-3-trimethylsilyltricyc...
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| Format: | Others |
| Language: | zh-TW |
| Published: |
2010
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| Online Access: | http://ndltd.ncl.edu.tw/handle/45693448550936540174 |
| Summary: | 碩士 === 輔仁大學 === 化學系 === 98 === 1-Bromo-2,2-dichloro-3-trimethylsilylcyclopropane (54) was the key precursor to synthesize the 1,3-fused tricyclic cyclopropanes. Cyclopropane 54 was treated with 1.5 equiv. methyllithium followed by reacting with cyclopentadiene to give 2-chloro-3-trimethylsilyltricyclo-
[3.2.1.02,4] oct-6-ene (64).
Compound 64 reacted with DPIBF to generate adduct 71. Treatment of 71 with TBAF in tetrahydrofuran affored diastereomeric mixture products 73 and 74. Treatment of 71 with TBAF in the presence of water gave adducts 75 and 76. Treatment of 71 with TBAF in furan yielded products 77 and 78. On the other hand, compounds 77 and 78 underwent the ring opening reaction to generate aldehyde 79.
Compound 64 reacted with thiophenol to give 2-chloro-3-trimethyl-
silyl-6-thiophenyltricyclo[3.2.1.02,4]octane (82). Treatment of 82 with TBAF in the presence of water gave 3-hydroxy-6-thiophenyltricyclo-
[3.2.1]octane (83).
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