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Denmark, Scott E. O'Connor, Stephen Patrick 2015-09-25T22:14:21Z 2015-09-25T22:14:21Z 10000-01-01 1998 1998 In mechanistic investigations, spectroscopic examinations and reaction surveys of substrate, reagent, and promoter were combined with solid-state evidence concerning the active form of the catalytically operative species to rationalize many of the observed features and trends of this system. Features illustrated to be critical for the best levels of stereocontrol were (1) formation of the ethylzinc alkoxide, (2) use of the Furukawa-Wittig reagent iodomethylzinc iodide, and (3) pretreatment of bis-sulfonamides such with diethylzinc. The single crystal, X-ray structure of a promoter-zinc compound revealed the likely mode of action of this species and verified its behavior as a divalent Lewis acid. A transition state rationale combining all of these features has been conceived and investigations to support this model have been conducted. Made available in DSpace on 2015-09-25T22:14:21Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 9904551.pdf: 16075642 bytes, checksum: ac050ffef0e93cc7c466e435166f79ec (MD5) Previous issue date: 1998 Embargo set by: Seth Robbins for item 85695 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 365 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1998. http://hdl.handle.net/2142/84414 (MiAaPQ)AAI9904551 eng Chemistry, Organic Catalytic, Enantioselective Cyclopropanation of Allylic Alcohols text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.