Carey, and Sundberg, Advanced Organic Chemistry, Part A fourth Edition, Chepter 13, \Photochemistry\, pp 743-789 \New insights into an old mechanism:

一. 对映异构 （一）分子的对称性 （二）含一个手性中心的分子

一. 诱导效应 二. 共轭体系

Allylic 1-3-Strain as a Controlling Element in Stereoselective Transformations TSO(2C)4 R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 2000, 39, 2054-2070 CH2)lOTs Conformation Design of Open-Chain Compounds

Acyclic Conformational Analysis-1 Ethane, Propane, Butane & Pentane Conformations Introduction to Allylic Strain Reading Assignment for week

Beak, P. (1992). “Determinations of transition-state geometries by the endocyclic restriction test: mechanisms of substitution at nonstereogenic atoms.” Acc. Chem. Res. 25: 215. The Primary Literature

Stereoelectronic Effects-1 Anomeric and Related Effects Electrophilic & Nucleophilic Substitution Reactions The SN2 Reaction: Stereoelectronic Effects Olefin Epoxidation: Stereoelectronic Effects Baeyer-Villiger Reaction: Stereoelectronic Effects Olefin Bromination: Stereoelectronic Effects

Dart Epoxides as Electrophiles Chem 206 Parker, R. E.; Isaacs, N. C. Chem. Rev. 1959, 59, 737-799. Rosowsky, A. In The Chemistry of Heterocyclic Compounds;

Prelog Strain: van der Waals interactions Baeyer Strain: bond angle distortion away from the ideal Pitzer Strain: torsional rotation about a sigma bond Baeyer Strain for selected ring sizes size of ring Ht of Combustion

Advanced Organic Chemistry Handout-09A Synthetic Mechanistic Overview of Electrophilic Halogenation andy ratz Evans group seminar, May 7, 1992 Matthew d. shair