Reactions of Unsaturated Azides; Part 27: [¹] Synthesis of 1,4-Diazidobuta-1,3-dienes

Abstract

Three different methods to prepare 1,4-diazidobuta-1,3-dienes are presented: nucleophilic substitution of electron-poor dichlorinated substrates, nucleophilic addition of hydrazoic acid at an electron-deficient diallene, and a sequence of prototropic isomerizations of propargyl sulfones followed by nucleophilic additions. In all cases, isolation and assignment of the diastereomeric products was possible, and some sequential reactions, such as reduction or 1,3-dipolar cycloaddition of the azido groups, were performed.

Key words

allenes - alkynes - azides - cycloaddition - dienes - isomerisation - nucleophilic addition - nucleophilic substitution

References

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11

The trans,trans structure of the higher-melting diastereoisomer of 7 was discussed,^¹² and the crystal and molecular structure of dimethyl trans,trans-2,5-dichloro-muconate was determined by single-crystal X-ray diffraction techniques.^¹³ In the latter case, however, neither the melting point nor other information on 7 including the method used to prepare this compound were given. Thus, the found (Z,Z)-configuration could not be assigned to the substances depicted in Scheme  [²] .