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Synthesis 1999; 1999(5): 859-863
DOI: 10.1055/s-1999-3461
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Thermolytic Fragmentation Reactions of Tricyclo[5.3.1.01,7]undeca-2,4-dien-10-one Tosylhydrazone under Basic Conditions

Mitsunori Oda* , Yoshimi Masaki, Shuichi Hayashi, Ryuta Miyatake, Shigeyasu Kuroda
  • *Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan; Fax +81(7 64)45 68 19; E-mail: oda@eng.toyama-u.ac.jp
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Publication Date:
31 December 1999 (online)

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Pyrolysis of tricyclo[4.3.1.01,7]undeca-2,4-dien-10-one tosylhydrazone (5) in the presence of base in an aprotic solvent gave the cyclic acetylene 6 and the allene 7, while that in the presence of sodium isopropoxide in isopropanol afforded the two isopropyl ethers, 8 and 9, along with 6 and none of 7. A dynamic process of methylene flipping in the acetylenic product 6 was also revealed.

Eschenmoser-Tanabe fragmentation - tosylhydrazone - dynamic process - cyclic acetylenes - allenes