Issue 0, 1971

Thiacycloheptadeca-3,8,10,15-tetrayne and thiacycloheptadeca-2,8,10,16-tetrayne-4,15-diol. Attempted synthesis of thia[17]annulene

Abstract

Cyclisation of di(octa-2,7-diynyl) sulphide by oxidation under Glaser conditions afforded thiacycloheptadeca-3,8,10,15-tetrayne, but attempted prototropic rearrangement of this compound to thia[17]annulene led to a complex mixture of products. Reaction of bis-sodioethynyl sulphide with hex-5-ynal gave bis-(3-hydroxyocta-1,7-diynyl) sulphide, which on Glaser cyclisation yielded thiacycloheptadeca-2,8,10,16-tetrayne-4,15-diol. The latter compound also gave a mixture on treatment with base or acid.

Article information

Article type
Paper

J. Chem. Soc. C, 1971, 1485-1488

Thiacycloheptadeca-3,8,10,15-tetrayne and thiacycloheptadeca-2,8,10,16-tetrayne-4,15-diol. Attempted synthesis of thia[17]annulene

W. Carruthers and M. G. Pellatt, J. Chem. Soc. C, 1971, 1485 DOI: 10.1039/J39710001485

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