Intermolecular Metal‐Free Cyclopropanation of Alkenes Using Tosylhydrazones | Zendy

Barluenga José | Zendy; Quiñones Noelia | Zendy; TomásGamasa María | Zendy; Cabal MaríaPaz | Zendy

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Intermolecular Metal‐Free Cyclopropanation of Alkenes Using Tosylhydrazones

Author(s) -

Barluenga José,

Quiñones Noelia,

TomásGamasa María,

Cabal MaríaPaz

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201200149

Subject(s) - cyclopropanation , chemistry , diazo , alkene , styrene , intermolecular force , organic chemistry , molecule , catalysis , copolymer , polymer

We describe the first general method for the metal‐free cyclopropanation of alkenes by using N ‐tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron‐deficient alkenes) by using N ‐tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K 2 CO 3 as a base to form the diazo species and is compatible with a wide array of functional groups.

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