Ring opening of 9: A solution of 9 (19.8 mg, 0.10 mmol) and galvinoxyl (2.0 mg, 4.7 mmol; added to prevent isomerization of the olefin geometries of the products) [21] in n-decane (50 mL) was placed in a screw-capped vial under a nitrogen atmosphere. The mixture was then stirred at 110 8C in an oil
Synthesis and Thermal Ring Opening of trans-3,4-Disilylcyclobutene
โ Scribed by Masahiro Murakami; Munehiro Hasegawa
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 238 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0044-8249
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โฆ Synopsis
In the reaction described by M. Murakami and M. Hasegawa on the following pages, the electronic effects are so dramatic that the sterically hindered substrate prefers to react by a more crowded pathway. This reaction will provide organic chemistry textbooks with a prime example of systems in which electronic effects are dominant over steric effects in determining the stereochemical outcome of a reaction.
๐ SIMILAR VOLUMES
## Abstract Ringโopening polymerization of the bicyclic lactone mixture **2**, __cis__/__trans__โ3โoxaโ4โoxoโ and __cis__/__trans__โ4โoxaโ3โoxobicyclo[5.4.0]undecane with Sn(Oct)~2~ as a catalyst was investigated for the first time (Scheme 1). The lactones were obtained by BaeyerโVilliger oxidation
Intramolecular carbene lnsertlon' In tiamantane could give rise, In prlnclple, to two different dehydrodlamantanes, the 1,3 (Ia) and 3,5 (To) isomers, by analogy with slmllar behavior m the adamantane2 and homoadamantanes series. In order to establish the course of this
The thermally induced ring opening of 1 and 5 proceeds with found, a behaviour that corresponds with the known photochemistry of cyclobutenes. A surprising reaction was high stereospecifity in a conrotatory fashion in agreement with the Woodward-Hoffmann rules. Upon flash pyrolysis of found if 1 and