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vi UST OF ABBREVIATIONS viii GENERAL INTRODUCTION I Dissertation Organization 2 CHAPTER 1. CHEMOSELECnvmVE LACTAM FORMATION IN THE ADDITION OF BENZENESULFONYL BROMIDE TO M-ALLYL ACRYLAMIDES AND A^-ALLYL 3,3-DIMETHYLACRYLAMIDES 3 Introduction 3 Results and Discussion 7 Addition of PhS02Br to A/^allyi Acrylamides 7 Addition of PhS02Br to A/^allyi 3,3-Diniethyl-acrylamides 10 Competition Experiments 11 Additions and Cyclizations Initiated by Other Electrophilic Radicals 14 Conclusions 20 Experimental Section 21 General Considerations 21 General Preparative Procedures and Compound Characterization 21 References 34 Appendix 37 CHAPTER n. LACTONE FORMATION IN THE ADDITION OF BENZENE­ SULFONYL BROMIDE TO DIENE AND ENYNE ESTERS 49 Introduction 49 Results and Discussion 52 Addition of PhS02Br to Acrylates 52 Competition Experiments 55 Addition of PhS02Br to P-Substituted Allyl Acrylates 59 iv Addition of PhSOaBr to Enyne Esters 70 Lactone Formation Initiated by Other Radicals 72 Conclusions 75 Experimental Section 75 General Considerations 75 General Preparative Procedures and Compound Characterization 75 References 95 Appendix 97 CHAPTER m. HOMOLYTIC BASE-PROMOTED AROMATIC ALKYLATIONS BY ALKYL HAUDES 145 Introduction 145 Results and Discussion 150 1.2-Disubstituted Benzenes 150 1.3-Disubstittuted Benzenes 154 1.4-Disubstituted Benzenes 157 Conclusions 160 Experimental Section 161 General Considerations 161 General Preparative Procedures and Compound Characterization 162 References 166 Appendix 168 CHAPTER IV. PREPARATION OF LEVOGLUCOSENONE AND ITS CHIRAL DERIVATIVES 17

Formation of [gamma]-lactams and lactones by radical cyclizations, homolytic aromatic alkylations, and preparation of levoglucosenone and its chiral derivatives