Electrophilic Additions to Ethylidenenorbornene and Vinylnorbornene | Zendy

T. C. Shields | Zendy

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Electrophilic Additions to Ethylidenenorbornene and Vinylnorbornene

Author(s) -

T. C. Shields

Publication year - 1971

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v71-188

Subject(s) - chemistry , peracetic acid , electrophile , double bond , 2 norbornyl cation , electrophilic addition , reactivity (psychology) , organic chemistry , ene reaction , medicinal chemistry , methanol , hydrogen peroxide , catalysis , medicine , alternative medicine , pathology

Electrophilic and free radical additions to 5-ethylidenebicyclo[2.2.1]hept-2-ene and 5-vinylbicyclo-[2.2.1]hept-2-ene have been carried out with peracetic acid, hydrogen chloride, and methanol. In contrast to chlorosulfonyl isocyanate, peracetic acid primarily attacks the exocyclic double bond in 5-ethylidenebicyclo[2.2.1]hept-2-ene. Several other electrophilic additions are discussed which demonstrate the unpredictable reactivity of the norbornyl system.

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