Kleine Ringe, 89. Eine alternative Synthese von Tetra-tert-butyltetrahedran

✍ Scribed by Maier, Günther ;Fleischer, Frank

• Book ID: 102367306
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 439 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199519950123

✦ Synopsis

Small Rings, 89. – An Alternative Synthesis of Tetra‐tert‐butyltetrahedrane

Cyclopropenyldiazomethane 3 is an ideal precursor for tetra‐tert‐butyltetrahedrane (6). Both, photochemical and thermal decomposition of 3 lead to cyclobutadiene 7, which can be photoisomerized to tetrahedrane 6. Tetra‐tert‐butyltetrahedrane (6) is also formed directly by a cheletropic cycloaddition of the carbenic center to the cyclopropene double bond in carbene 4. This is the first example for the synthesis of a tetrahedrane, which does not occur via the corresponding cyclobutadiene. The formation of pyridazine 10 dominates the thermolysis of 3. Azete 12 is obtained both by photolysis as well as by thermolysis of Dewar‐pyridazine 11, the irradiation product of 10.