Interrupted carbonyl-olefin metathesis via oxygen atom transfer | Zendy

Jacob R. Ludwig | Zendy; Rebecca B. Watson | Zendy; Daniel J. Nasrallah | Zendy; Joseph B. Gianino | Zendy; Paul M. Zimmerman | Zendy; Ren A. Wiscons | Zendy; Corinna S. Schindler | Zendy

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Interrupted carbonyl-olefin metathesis via oxygen atom transfer

Author(s) -

Jacob R. Ludwig,

Rebecca B. Watson,

Daniel J. Nasrallah,

Joseph B. Gianino,

Paul M. Zimmerman,

Ren A. Wiscons,

Corinna S. Schindler

Publication year - 2018

Publication title -

science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 12.556

H-Index - 1186

eISSN - 1095-9203

pISSN - 0036-8075

DOI - 10.1126/science.aar8238

Subject(s) - chemistry , intramolecular force , oxetane , reactivity (psychology) , olefin fiber , metathesis , catalysis , organic chemistry , photochemistry , polymerization , polymer , medicine , alternative medicine , pathology

Two ways out of an oxetane Oxetanes are highly reactive four-membered rings that contain three carbon atoms and an oxygen atom. Recently, they were implicated as transient intermediates in Lewis acid–catalyzed intramolecular metathesis reactions of ketones with olefins. Ludwiget al. now report that by replacing the Lewis acid with a strong Brønsted acid, they can change the course of the oxetane ring-opening. In a so-called interrupted metathesis, the oxygen atom migrates and then departs through dehydration, while the remaining carbon framework cyclizes to form tetrahydrofluorene compounds.Science , this issue p.1363

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