PAPER www.rsc.org/obc Organic & Biomolecular Chemistry Facial selectivity in the 4 + 2 reactions of a diene derived from carvone (2005)

Content Provider	CiteSeerX
Author	Morrison, Christopher F. D. Jean Burnell*a. Vaters, A. Jamie P. Millera, A. David O.
Abstract	The facial selectivities of cyclohexadienes bearing isopropenyl and isopropyl groups as plane-nonsymmetric substituents were assessed in 4 + 2 reactions with N-phenylmaleimide, tetracyanoethylene and 4-phenyl-1,2,4-triazoline-3,5-dione. The only adducts were those arising by attack of the dienophile on the face of the diene opposite the isopropenyl or isopropyl group. In spite of some mechanistic similarities that tetracyanoethylene and 4-phenyl-1,2,4-triazoline-3,5-dione might have with the 4 + 2 addition of singlet oxygen, these dienophiles show none of the ability that singlet oxygen has shown to add syn to a plane-nonsymmetric isopropyl group.
File Format	PDF
Publisher Date	2005-01-01
Access Restriction	Open
Subject Keyword	Plane-nonsymmetric Isopropyl Group Plane-nonsymmetric Substituents Singlet Oxygen Isopropyl Group Facial Selectivity Mechanistic Similarity
Content Type	Text