Thiacycloheptadeca-3,8,10,15-tetrayne and thiacycloheptadeca-2,8,10,16-tetrayne-4,15-diol. Attempted synthesis of thia[17]annulene
作者:W. Carruthers、M. G. Pellatt
DOI:10.1039/j39710001485
日期:——
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
在Glaser条件下通过氧化使二(八-2,7-二炔基)硫化物环化,可得到3,8,10,15-丁炔三环杂庚酸酯,但尝试将该化合物进行质子重排,使其成为硫杂[17]环戊烯,从而形成复杂的混合物。产品。双-二乙炔基硫醚与5--5-己烯基的反应生成双-(3-羟基辛基-1,7-二炔基)硫化物,在格拉塞尔环化反应中生成噻二环庚基-2,8,10,16-四炔-4,15-二醇。后一种化合物在用碱或酸处理后也得到了混合物。