Date of Completion


Thesis Type

College of Arts and Science Honors



First Advisor

Rory Waterman


phosphinidene, low-valent, phosphorus, catalysis, porphyrin


A class of transition-metal and main group compounds will be synthesized and investigated for their hypothesized propensity for main group bond formation via low-valent fragment transfer. Low-valent fragments are reactive species that can insert into various elemental bonds, and methods to generate these reactive intermediates represent fundamentally important synthetic methodologies. It is proposed here that catalytic routes to generate and transfer phosphinidenes may be optimized by utilizing transition-metal and main group compounds bearing differing steric and electronic ligands. The work here is expected to expand upon main group bond formation via new catalysts, phosphinidene sources, and alkene/diene “traps,” based on known phosphinidene literature and successes in catalytic endeavors by other research groups. The development of phosphinidene chemistry is closely related to the carbenes, a paramount synthon capable of numerous insertion and cycloaddition processes.

Experimental advances in this work aim to reduce waste production by generating newer routes to creating small phosphorus containing molecules, not dissimilar from that of known hydrophosphination products, but with greater chemical functionality, for example as use in pre-ceramic semiconducting materials. The results of this work were largely unsuccessful, though indicated that some success is possible using similar routes, perhaps with varied starting materials or experimental setup. Ideally, future work in this field will present researchers with a greater understanding of the nature of these phosphinidene fragments, creating a foreseeable future in sustainable medicine and polymer production containing phosphorus.

Available for download on Saturday, May 04, 2024