Michael P. Cava

Thermolytic removal of t-butyloxycarbonyl (BOC) protecting group on indoles and pyrroles

The t-Butyloxycarbonyl (BOC) group on indoles and pyrroles can be removed cleanly and in high yield by simple thermolysis: no acid, no base, no solvent is required.

‘Organic metals’: alkylthio substitution effects in tetrathiafulvalene–tetracyanoquinodimethane charge-transfer complexes

The synthesis and diverse conductivity properties of the tetracyanoquinodimethane (TCNQ) complexes of several tetrakis-(alkylthio)-tetrathiafulvalenes are described, and compared with those of tetrathiafulvalene-TCNQ and related complexes.

Functionalization Of 3,4-Ethylenedioxythiophene

Syntheses of 3,4-ethylenedioxythiophene-based vinylenes and oligomers are reported.

Organotellurium Compounds 5. A Convenient Synthesis of Some Aliphatic Ditellurides

Abstract Although diethyl dielluide was first obtained about 130 years ago,1 the aliphatic ditelluides have been relatively little studied. This is party due to the extremely repulsive odors of the lowest members of the series, but also to the fact that the known methods of synthesis are not practical for the preparation of large amounts of pure materials.2 Fo example, din-butyl ditelluride (1), the first well characterized dialky 1 dielluride, was obtained from Na2Te2 and n-butyl bromide in only 23% yeild after fractional distillation from the corresponding monotellurie.3.

A convenient synthesis of t-butyldimethylsilyl protected cyanohydrins

Abstract A simple high yielding procedure is described for the direct conversion of aldehydes to t-butyldimethylsilyl (TBS) protected cyanohydrins using TBSCl, KCN and ZnI2.

A total synthesis of dragmacidin B

Abstract A simple total synthesis of dragmacidin B is described. This constitutes the first synthesis of a member of the 2,5-bis(3′-indolyl)piperazine family of marine alkaloids. The didebromo analog of dragmacidin B was also prepared.

Furan- and pyrrole-containing analogs of α-quinquethiophene: spectroscopic and electrochemical properties

Abstract A series of pentacyclic analogs of α-quinquethiophene containing one or two furan or pyrrole units has been synthesized. The synthesis is based on the cyanide-catalyzed Stetter reaction, providing the ketonic precursors to the pentacycles. Spectral and electrochemical investigations show that the redox-stable mixed pentacycles display hypsochromic shifts in their absorption maxima, as well as a greater ease of oxidation, in comparison to α-quinquethiophene.

Synthesis of mixed thiophene-pyrrole heterocycles

The synthesis of mixed thiophene-pyrrole heterocycles has been reviewed. The systems under consideration are various isomeric thienylpyrroles as well as tricyclic analogs containing non-condensed combinations of two or three pyrrole and thiophene units

Electrochemical studies of fused-thiophene systems

Abstract A study of the electrochemical polymerization of two and three fused thiophene-ring systems is presented. Thieno[2,3-b]thiophene (TT) and dithieno[3,2-b; 2′,3′-d]thiophene (DTT) can be polymerized electrochemically on conducting glass (SnO 2 ) or Pt. Poly DTT can be electrochemically oxidized and reduced between the neutral and acceptor doped forms, while poly TT does not show a reduction wave after oxidation. Observed u.v. absorption spectra of poly DTT as a function of oxidation potential resemble that of polythiophene. The complex impedance of poly DTT indicates a decrease in charge transfer resistance as the oxidation potential increases. The limiting capacitance is shown to be closely correlated to the doping level of the polymer.

Synthetic applications of dimethyl(methylthio)sulfonium fluoroborate: sulfenyletherification and sulfenyllactonization

Abstract A new method for the formation of cyclic ethers and lactones is described. Dimethyl(methylthio)sulfonium fluoroborate (DMTSF) initiates formation of an episulfonium ion, which is followed by internal nucleophilic displacement to give the products in good yields.