A Straightforward Access to Mono- and Bis(pyrrolo)tetrathiafulvalenes

Abstract

An alternative efficient synthetic procedure to mono- and bis(pyrrolo)tetrathiafulvalenes is proposed starting from 4,4-diethoxybut-2-ynal.

acetals - ring closure - pyrroles - tetrathiafulvalene - 4,4-diethoxybut-2-ynal

References

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<A NAME="RZ07706SS-11">11</A>

Attempts to purify imine 4 by silica gel or alumina chromatography invariably led to a partial reverse reaction to the starting products.

<A NAME="RZ07706SS-12">12</A>

Alternatively, compound 5 may be directly engaged in the following step without being chromatographed (no noticeable loss in the yield of 6). In fact, the purification of 5 by silica gel chromatography is accompanied by formation of compound 6.

<A NAME="RZ07706SS-13">13</A>

We observed lower yields with longer times.