By Alan R. Katritzky, Richard J. K. Taylor and Gary Molander
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Additional info for Comprehensive Organic Functional Group Transformations II: v. 4(Carbon with Two Heteroatoms, Each Attached by a Single Bond)
L. Bernad, J. A. Pe´rez-Andre´s, Tetrahedron Lett. 1998, 39, 1409–1412. 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.
Interestingly, the corresponding (E)-haloalkenes are obtained under anhydrous conditions. Simple 1,1,2-triiodo compounds can be prepared by treatment of the corresponding vinylstannane with iodine in carbon tetrachloride (Equation (115)) <2001JACS1768>. O OH O HO H NIS, cat. 4 21 Diiodoalkanes from Alkynes As is well documented in the literature, 2 equiv. of hydrogen iodide adds to terminal alkynes to produce diiodoalkanes (see Hill (COFGT 1995)). In this case, diiodination occurs at the internal alkynyl carbon (Equation (116)).
Molander at University of Pennsylvania, he joined Procter & Gamble Pharmaceuticals in 2002. His scientific interests include green chemistry, organometallic reagents, natural product synthesis, and medicinal chemistry. # 2005, Elsevier Ltd. 02 Functions Incorporating a Halogen and a Chalcogen N. W. A. 2 -Haloalkyl haloformates—R12CHalOCOHal and carbonate derivatives— R12CHalOCOOR2, etc. 2 HALOGEN AND SULFUR DERIVATIVES—R12CHal(SR2), etc. 2 Other dicoordinate -halosulfur derivatives—R2CHal(SX), etc.