29041-32-5Relevant articles and documents
Samarium(II) Diiodide Mediated Coupling of Bis(bromomethyl)arenes. Facile Synthesis of n>Cyclophanes without using High-Dilution Techniques
Takahashi, Senji,Mori, Nobuo
, p. 2029 - 2032 (2007/10/02)
In the presence of samarium(II) diiodide (Sml2), coupling of 1,3- and 1,4-bis(bromomethyl)benzenes proceeds smoothly to give their cyclic and acyclic oligomers.Use of 1.2 equiv. of Sml2 gives 1,2-bis(3- and 4-bromomethylphenyl)ethanes, respectively, in 95percent yield, and the use of 5.0 equiv. of Sml2 affords n>metacyclophanes and n>paracyclpphanes (n = 2, 3 and 4), respectively, in satisfactory yields.By using 5.0 equiv. of Sml2, 2-bromo- and 2-methoxy-1,4-bis(bromomethyl)benzenes and 1,4- and 2,6-bis(bromomethyl)naphthalenes each give only one of several expected isomeric cyclophanes as the major cyclic oligomer.
Transanular Interactions in Phanes, 26. Models for Excimers: Achiral and Chiral(2,6)Naphthalinophane
Blank, Norman E.,Haenel, Matthias W.
, p. 827 - 832 (2007/10/02)
The achiral(2,6)naphthalenophane diastereomer 1 which was not obtained previously, was synthesized by using dibromo-substitution to force the formation of 3 besides 4 in the vacuum pyrolysis of the disulfone 12.Debromination of 3/4 via halogen-metal-exchange followed by hydrolysis gave a mixture of 1/2 from which 1 could be isolated and characterized.