During this semester, ten reactions were carried out. The first was the synthesis of D-glyceraldehyde acetonide from D-mannitol. The next six reactions were involved with the synthesis of the corresponding γ-lactone of glyceraldehyde acetonide. The final three reactions were attempted syntheses of ethyl ethynyl ether, the key starting material in the synthesis of TMS ketene. Introduction In the...

Some new mono-and bis-polycyclic aromatic spiro-beta-lactams and bis-non spiro-polycyclic aromatic beta-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including 1H-NMR, 13C-NMR, ...

Photolysis of S,C-sulfonium ylides derived from thioanisol, thiophene, benzothiophene, or dibenzothiophene provides products deriving from dicarbomethoxycarbene. In methanol, no rearrangement of the carbene to the ketene derivative is observed. Formation of dibenzothiophene and benzothiophene is quantitative. For the thiophene-based ylide, insertion of the carbene into the alpha-CH bond of thio...

It is shown that the N-(p-ethoxyphenyl) group on beta-lactams can be oxidatively removed by ceric ammonium nitrate in good yield. Fourteen new N-(p-ethoxyphenyl)-2-azetidinones 8a-n were synthesized through standard [2+2] ketene-imine cycloadditions (Staudinger reaction). Treatment of these compounds with ceric ammonium nitrate yielded the N-dearylated 2-azetidinones 9a-n in good to excellent y...

Abstract Yndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into regio­selective addition Brønsted acids to non-symmetric yndi...