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By W. Horspool, F. Lenci

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Another available pathway in the case of iodides is transfer of an iodine atom from a molecule of unreacted starting material. Halogen atom transfer occurs readily for alkyl iodides (k ≈ 2 × 105 mol–1 sec–1)25 and accounts for the observed interconversion of iodides 64a (Scheme 3). In the more viscous solvent (CH3)3COH, in which escape from the radical cage (6) occurs more slowly, there is substantially less epimerization. In contrast with that for iodides, halogen atom transfer is much slower for alkyl bromides (k ≈ 6 × 102 mol–1 sec–1),25 permitting combination/disproportionation to compete.

13. , Photochemistry of alkyl halides. 4. 1-Norbornyl, 1-norbornylmethyl, 1- and 2-adamantyl and 1-octyl bromides and iodides, J. Am. Chem. , 98, 8135, 1976. 14. Leuf, W. , Synthese von 1-hydroxynorbornen aus norcampher, Chimia, 36, 81, 1982. 15. , Direct photolysis of 1-halo-1-hexynes. Lack of ionic behavior, J. Org. , 48, 1732, 1983. 16. , The Photochemistry of Alkyl Dihalides. Part I: Geminal Dihalides. D. dissertation, University of North Carolina, Chapel Hill, 1978. 17. , Photochemistry of alkyl halides.

The problem in this case is angle strain. 23 By contrast, irradiation in CH3OH readily afforded ether 53 (R = CH3), along with smaller amounts of the reduction product norbornane (9), the unprecedented 1,3-elimination product 54 and the rearrangement products 55–57. The 2-chloro derivatives 58 underwent syn,anti interconversion in competition with formation of the reduction product 60, the ethers 61 and 63, and the 1,3-elimination product 62. fm Page 8 Tuesday, August 12, 2003 6:52 PM 1-8 CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition with methanolic AgNO3 resulted in ionization of the more reactive chlorine substituent to afford ethers 59.

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