Synthesis, structure, reactivity, and diastereoisomer separation of (Tropone)fe(co)2l complexes (l = pph3, (+)-neomenthyldiphenylphosphine)

James A.S. Howell, Adrian D. Squibb, Zeev Goldschmidt, Hugo E. Gottlieb, Amlra Almadhoun, Israel Goldberg

Research output: Contribution to journalArticlepeer-review

Abstract

The title complexes have been prepared by amine oxide substitution of (tropone)Fe(CO)3. The solid-state molecular structure of (tropone)Fe(CO)2PPh3 reveals a distorted-square-pyramidal geometry with a basal PPh3 trans to the keto-substituted C═C bond; in solution, both basal isomers are populated. Rates of normal and inverse electron demand cycloaddition, and of sigmahaptotropic rearrangement, are much enhanced relative to those for the tricarbonyl. The (tropone)Fe(CO)2((+)-neomenthyldiphenylphosphine) diastereoisomer of 6S planar chirality may be isolated by crystallization. Though the rate of the 1,3-shift is enhanced relative to that for the tricarbonyl, normal and inverse electron demand cycloadditions and electrophilic attack proceed under mild conditions without racemization of the planar chirality.

Original languageEnglish
Pages (from-to)80-91
Number of pages12
JournalOrganometallics
Volume9
Issue number1
DOIs
StatePublished - 1990

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