Ronald L. Blankespoor

Polymerized 3-methoxythiophen. A processable material for the controlled release of anions

The electrochemical oxidation of 3-methoxythiophene at a glassy carbon electrode produces a film of a processable conductive material that is used for the controlled release of the neurotransmitter glutamate.

Photochemical synthesis of 3-alkynals from 1-alkynoxy-9,10-anthraquinones.

Photolysis of 1-(3-alkynoxy)-9,10-anthraquinones in deoxygenated methanol leads to moderate yields (35-45%) of 3-alkynals along with the unexpected formation of diacetals. Reaction of these 3-alkynals with Grignard and Wittig reagents occurs nearly quantitatively without rearrangement to their 2,3-dienal isomers.

Chemistry of 3-Alkynals. A Review

Introduction ..........................................................................................468 I. Synthesis of Unsubstituted 3-Alkynals ................................................469 1. Hydrolysis of Enol Ethers .....................................................................469 2. Hydrolysis of Acetals ............................................................................469 3. Dess-Martin Periodinane Oxidation ......................................................469 4. TEMPO/PhI(OAc)2 Oxidation ..............................................................470 5. Periodate Cleavage of Glycols ...............................................................470 6. Photochemically from 1-Alkynoxy-9,10-anthraquinones.........................471 II. Stability of Unsubstituted 3-Alkynals .................................................471 III. Reactions of Unsubstituted 3-Alkynals ...............................................472 1. Grignard Addition ................................................................................472 2. Wittig Addition .....................................................................................472 3. Organocerium Addition ........................................................................472 4. Enolate Formation ...............................................................................473 5. Acetal Formation..................................................................................473 6. Cyanide Addition..................................................................................473 IV. Reactions and Synthesis of 2,2-Disubstituted 3-Alkynals ..................474 Conclusion .............................................................................................475 Acknowledgment...................................................................................475 References..............................................................................................476