By W. Horspool, F. Lenci
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Chem. , Perkin Trans. 2, 1397, 1982. 3. , Photobehavior of alkyl halides in solution: radical, carbocation and carbene intermediates, Acc. Chem. , 17, 131, 1984. 4. , Wiley, London, 1973, chap, 11; (b) Grimshaw, J. , Photochemistry and photocyclization of aryl halides, Chem. Soc. , Recent advances in the photochemistry of the carbon–halogen bond, in The Chemistry of Functional Groups, Supplement D, Patai, S. , Wiley, London, 1983, chap. J. , Photosolvolyses and attendant photoreactions involving carbocations, Org.
Photochemistry of alkyl halides. 12. Bromides vs. iodides, J. Am. Chem. , 113, 2709, 1991. 8. B. , Photooxidation of ethyl iodide at 22˚C, J. Phys. , 85, 2691, 1981. fm Page 29 Tuesday, August 12, 2003 6:52 PM Photobehavior of Alkyl Halides 1-29 9. , Isomerization in the photolysis of alkyl iodides, J. Am. Chem. , 76, 6263, 1954. 10. , Jr. , 6267, 1966. 11. S. , Photochemistry of alkyl halides. II. Support for an electron transfer process, J. Am. Chem. , 96, 7142, 1974. 12. T. , Free carbonium ions, in Carbonium Ions, Vol.
19 The 1,4-diiodide 38 afforded the mono- and disubstituted derivatives 39 and 40 in CH3OH and wet CH3CN. 13,20 The greater ease of forming the 1-adamantyl, compared with the 1-norbornyl, cation is reflected in the higher ratio of ionic to radical product from both the iodide and bromide. 13 Adamantyl bromides are significantly more sensitive to the presence of electron-withdrawing substituents than are the corresponding iodides. 21 hν X 41a, X = I b, X = Br H ROH + 42 CH 3OH (CH 2OH)2 OR 43 X= I Br 14% X= I Br 6% 99% 53% 98% 83% X Br X X 44a, X = I b, X = Br c, X = OCH 3 Br X X Br X 45a, X = I b, X = Br c, X = OCH 3 X X 46 47a, X = I b, X = Br c, X = NHC(O)CH 3 Nonbridgehead Halides: Elimination vs.