SYNTHETIC APPLICATIONS OF ALLENES IN ORGANIC CHEMISTRY

异氰酸酯、卡宾和氮烯与 取代的丙二烯基硫醚将用于生成 α-亚烷基-β-内酰胺、亚甲基环丙烷和 亚甲基氮杂环丙烷。 β-内酰胺将用于制备 基于作用机制的单环β-内酰胺酶抑制剂。 亚烷基 功能性将在稳定初始酰基酶中起关键作用 中间体 α-亚乙烯基（即环外丙二烯基）β-内酰胺将 也可制备和检测（β-内酰胺酶抑制活性）， 它们的NU-磺酸盐衍生物。 高度紧张的亚甲基环丙烷和 亚甲基氮杂环丙烷将通过分子内加成产生 碳烯和氮烯到选定的联烯。 预期 由此产生的三亚甲基甲烷型中间体将 分子内捕获，产生有用的双环和三环体系。 手性丙二烯基亚砜将通过2，3-σ-转移反应制备 容易获得的手性炔丙醇的重排。 这些 材料将用于制备手性β-内酰胺，并探索 联烯基阴离子的构型稳定性。

The cycloaddition reactions of isocyanates, carbenes, and nitrenes with substituted allenyl sulfides will be used to generate Alpha-alkylidene-Beta-lactams, methylenecyclopropanes, and methyleneaziridines respectively. The Beta-lactams will be used to prepare mechanism-based monocyclic Beta-lactamase inhibitors. The alkylidene functionality will serve a key role in stabilizing the initial acyl-enzyme intermediate. Alpha-Vinylidene (i.e. exocyclic allenyl) Beta-lactams will also be preapared and tested (for Beta-lactamase inhibitory activity) as their Nu-sulfonate derivatives. Highly strained methylenecyclopropanes and methyleneaziridines will be generated via the intramolecular addition of carbenes and nitrenes to selected allenes. The expected trimethylenemethane-type intermediates thereby produced will be intramolecularly trapped generating useful bi- and tricyclic systems. Chiral allenyl sulfoxides will be prepared via 2,3-sigmatropic rearrangement of the readily available chiral propargylic alcohols. These materials will be used to prepare chiral Beta-lactams and to explore the configurational stability of allenyl anions.