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By Alan R. Katritzky, Richard J. K. Taylor and Gary Molander

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Extra resources for Comprehensive Organic Functional Group Transformations II: v. 4(Carbon with Two Heteroatoms, Each Attached by a Single Bond)

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G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, J. Chem. , Chem. Commun. 1999, 215–216. L. Aufauvre, P. Knochel, I. Marek, J. Chem. , Chem. Commun. 1999, 2207–2208. M. Tamura, H. Quan, A. Sekiya, Eur. J. Org. Chem. 1999, 3151–3153. T. Itoh, K. Sakabe, K. Kudo, H. Ohara, Y. Takagi, H. Kihara, P. Zagatti, M. Renou, J. Org. Chem. 1999, 64, 252–265. S. Sendelbach, R. Schwetzler-Raschke, A. Radi, R. Kaiser, G. H. Henle, H. Korfant, S. Reiner, B. Fo¨hlisch, J. Org. Chem. 1999, 64, 3398–3408. K.

Van Der Puy, T. R. Demming, G. V. B. Madhavan, A. Theneppan, H. S. Tung, J. Fluorine Chem. 1996, 76, 49–54. M. A. Avery, P. Fan, J. M. Karle, J. D. Bonk, R. Miller, D. K. Goins, J. Med. Chem. 1996, 39, 1885–1897. T. Yamashita, J. Org. Chem. 1996, 61, 6438–6441. 24 1996S259 1996SL529 1996SL693 1996T503 1996TL4085 1997SC2865 1997SL606 1997T557 1997TL3395 1998EJO919 1998JCS(P1)3145 1998SC1667 1998T1029 1998TL1409 1999CC215 1999CC2207 1999EJO3151 1999JOC252 1999JOC3398 1999JOC6717 1999JOC7048 1999JOM(572)31 1999SC4015 1999SC4101 1999TL1459 2000CFB885 2000CL1180 2000JOC4830 2000JOC6547 2000JFC(102)317 2000JSC(P1)1187 2000OL247 2000OL563 2000S139 2000SL89 2000T3539 2000T1369 2000TL579 2000TL9357 2001AC(206)19 2001AG(E)2326 2001JACS5925 2001CL222 2001JACS1768 2001JFC(109)39 2001JOC1216 2001JOM(624)316 2001OL2713 2001OL2859 2001OL3103 2001T4925 2001TL999 2001TL1999 2001TL2901 2001TL3555 2002ZOR(E)902 2002AG(E)351 2002JACS2456 2002JFC(116)65 2002JOC5369 2002JOC7303 Dihaloalkanes, R1R2C(Hal)2 H.

Methods for direct benzylic halogenation of tolylamines are unknown. Nevertheless, benzylic gem-dibrominations have been achieved by preparing the succinimide derivative of the corresponding tolylamine followed by treatment with molecular bromine <2002S221>. Dihaloalkanes, R1R2C(Hal)2 15 The synthetic sequence produces the desired gem-dibromo compound in excellent yield (Equation (80)). In addition, simple changes to the reaction conditions lead to benzylic monobromination product exclusively. ), CCl4, reflux, 8 h N CH3 ð80Þ N 94–96% CHBr2 O O Complex mixtures of mono-, di-, and tribrominated products are not uncommon when preparing ,-dibromoketones from the corresponding alkyl ketone.

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