The synthesis of 3-substituted-3-(trimethylsilyl)cyclopropenes (X = CO2Et, CHO, CN) is described. Their acid sensitivity and thermal stability was probed and the reaction products were identified. In one case, a novel rearrangement to a Dewar furan maybe involved and this pathway was explored via ki
1-Chloro-3-trimethylsilylcyclopropene--A new synthesis of 3,3′-bicyclopropenyl
✍ Scribed by Gon-Ann Lee; Chi-Sheng Chen
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 170 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
3,3'-Bicyclopropenyl (1) was synthesized from a new isomer 3 of 1 -chloro-2-(2-chloro-3-trimethylsilyicycloprop-1 -yl)-3-trimethylsilylcyclopropanes, which was formed by ene dimerization of 1-chloro-3-trimethylsilylcyclopropene (2) foUowed by reduction with diimide. Compoumd 2 was generated by debromochlorination of 1-bromo-2,2-dichloro-3-tfimethylsilylcyclopropane (4) which was synthesized by dichlovocarbene addition of [3-bromovinyl uimethylsilane.
📜 SIMILAR VOLUMES
It has been demonstrated that 7,7-dichlorobicyclo[4.l.O]hept-3-enes are excellent precursors to benzocyclopropenes. l-4 We report here an application of this method to the synthesis of the functionalized benzocyclopropenes 1 and 2, potential precursors to cyclopropabenzynes 3 and 4.
3-Methyl-3-trimethylsilylcyclopropene (1) was preparedby reacting(.Z)-3-trimethy lsilyl-2-butenylcbloride (5) with sodiumamide. This compound(1) was convertedto l,2-dibenzoyl-3 -metiyl-3-trimethyIsilylcyclopro~ne(2), a rare exampleof an isolablecyclopropenewith two electronwithdrawinggroupsat the vi