Radical Addition of SF5Cl to Cyclopropenes: Synthesis of (Pentafluorosulfanyl)cyclopropanes | Zendy

Gauthier Lefebvre | Zendy; Olivier Charron | Zendy; Janine Cossy | Zendy; Christophe Meyer | Zendy

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Radical Addition of SF₅Cl to Cyclopropenes: Synthesis of (Pentafluorosulfanyl)cyclopropanes

Author(s) -

Gauthier Lefebvre,

Olivier Charron,

Janine Cossy,

Christophe Meyer

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01840

Subject(s) - chemistry , substituent , chlorine atom , chlorine , medicinal chemistry , adduct , carbon atom , radical , carbon fibers , photochemistry , free radical addition , organic chemistry , ring (chemistry) , materials science , composite number , composite material

With the goal of accessing yet unknown SF 5 -cyclopropyl building blocks, the radical addition of SF 5 Cl to cyclopropenes was investigated. Addition of the SF 5 radical occurs regioselectively at the less substituted carbon of cyclopropenes and rans o the most hindered substituent at C3, while chlorine atom transfer proceeds with moderate to high levels of diastereocontrol. The carbon-chlorine bond in the resulting adducts can undergo subsequent radical reduction or be involved in a radical cyclization.

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