Synthesis of cyclodeca-1,5-diyne derivatives having o-nitrophenylseleno group.

7-Benzoyloxy-3-(2-nitrophenylseleno)-1,5-cyclodecadiyne (13) was prepared from 5-hexyn-1-ol and propargyl bromide via 10-iodo-7-(t-butyldiphenylsiloxy)-5,9-decadiynal (10). The facile cyclization of the acyclic precursor 10 would be rationalized in terms of "bulky group (TBDPSO) assisted conformational control". Oxidation of 13 by NaIO4, followed by thermal treatment gave tetrahydronaphthalene derivative 15, indicating the generation of biradical.