Ying Liu


The use of pre-heated silica gel and alumina along with a chlorinating agent, generates HC1 in situ, which has been found to add to norbornadiene ( IX ). Treated in this fashion, norbornadiene readily results in the formation of two isomers, exo-5- chloronorbornene ( XI ) and 3-chloronotricyclene ( XII ) at room temperature in methylene chloride, with ejco-5-chloronorbornene being the predominant product ( 70% 1% ). In promoting the hydrohalogenation reaction, silica gel was found to be less efficient compared to alumina, but undesired diadducts appeared to be less prominent when silica gel rather than alumina was used. Deuterated alumina and thionyl chloride in methylene chloride solution was found to result in the addition of DC1 to norbornadiene. Three deuterated products: 29% exo,ejco-6-chlorobicyclo[2.2.1]hept-2-ene-5-d ( XVII ), 14% ea,5>7i-5-chlorobicyclo[2.2.1]hept-2-ene-7-d ( XVTIa ) and 19% 5- chlorotricyclo['6]heptane-3-d ( XV111 ), as well as the two undeuterated products, 27% ejco-5-chloronorbornene ( XI ) and 11% 3-chloronotricyclene ( XII ), were detected by GC/MS analysis. A higher ratio of XVU/XVlla for the catalyzed DC1 addition over the uncatalyzed addition suggests that the surface of the alumina somewhat slowed Wagner-Meerwein rearrangement during this reaction. *See document for exact formulas

Library of Congress Subject Headings

Alkenes; Silica-alumina catalysts; Halogenation; Silica gel; Aluminum oxide; Surface chemistry

Publication Date


Document Type


Department, Program, or Center

School of Chemistry and Materials Science (COS)


Morrill, Terence


Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works. Physical copy available through RIT's The Wallace Library at: QD305.H7 L58 1999


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