Chellappan, Sheela Kochuparambil; Haberhauer, Gebhard; Feuerbacher, Sven; Rominger, Frank; Oeser, Thomas; Gleiter, Rolf:
Synthesis and properties of 1,6-difunctionalized cyclodeca-3,8-diynes.
2003
In: Synthesis, Heft 3, S. 431 - 435
Artikel/Aufsatz in Zeitschrift2003Chemie
Titel:
Synthesis and properties of 1,6-difunctionalized cyclodeca-3,8-diynes.
Autor(in):
Chellappan, Sheela Kochuparambil; Haberhauer, GebhardLSF; Feuerbacher, Sven; Rominger, Frank; Oeser, Thomas; Gleiter, Rolf
Erscheinungsjahr
2003

Abstract:

The reaction of tert-Bu acetate with 1,4-dibromobut-2-yne in the presence of LDA yielded 1,6-di(tert-butyl)cyclodeca-3,8-diyne-1,6-dicarboxylate (I). The 1,6-di(tert-butyl) groups of I were transferred to bis(hydroxymethyl), bis(bromomethyl) (II) , bis(cyanomethyl), dicarbaldehyde, and bis(methoxyvinyl) groups. In case of II the two diastereomers [cis(a,e), trans(a,a)] were sepd. From cis-II and a trans-biscyanide compd. (III) we were able to obtain detailed structural parameters by means of X-ray crystallog. By means of temp. dependent NMR spectroscopy of III we estd. the activation energy for the chair-boat conversion to be 10.5 kcal/mol.