scholarly journals CYCLOADDITIONS OF DIAZOALKMTES TO VINYL AND ALLYL SULFIDE SYSTEMS

1972 ◽  
Vol 1 (9) ◽  
pp. 771-774 ◽  
Author(s):  
Kiyosi Kondo ◽  
Iwao Ojima
Keyword(s):  
1995 ◽  
Vol 14 (11) ◽  
pp. 5450-5453 ◽  
Author(s):  
Yoshinori Miyauchi ◽  
Saisuke Watanabe ◽  
Hitoshi Kuniyasu ◽  
Hideo Kurosawa

1987 ◽  
Vol 16 (10) ◽  
pp. 1967-1970 ◽  
Author(s):  
Takeshi Takeda ◽  
Shinji Ogawa ◽  
Nagaaki Ohta ◽  
Tooru Fujiwara
Keyword(s):  

1991 ◽  
Vol 14 (4) ◽  
pp. 364-369
Author(s):  
Hokoon Park ◽  
Nam Hoon Baik ◽  
Jae Yeol Lee ◽  
Soo Ja Kim ◽  
Won Hoon Ham

1949 ◽  
Vol 22 (1) ◽  
pp. 1-7
Author(s):  
M. L. Selker

Abstract The work described here is an extension of the study of the reaction of methyl iodide with sulfur compounds originally begun with the purpose of using such data in determining the sulfur linkage in vulcanized rubber. A previous paper dealt with the reactions of methyl iodide with propanethiol, propyl sulfide, propyl disulfide, allyl sulfide, and thiophene. This article adds to the list, n-butyl methallyl sulfide, allyl disulfide, allyl tetrasulfide, n-propyl tetrasulfide, and trithiane. The removal of combined sulfur from vulcanized rubber as trimethylsulfonium iodide on treatment with methyl iodide at room temperature was persuasive evidence of the presence of sulfide sulfur linked to allylic type residues. The evidence offered, however, did not constitute exclusive proof because it was not known whether still other types of sulfur linkage would also yield trimethylsulfonium iodide. To shed more light on this question, the sulfur linkages most likely to occur in vulcanizates—the allyl-alkyl monosulfide, diallyl and dialkyl di- and polysulfide—were investigated. The trithiane reaction is of interest mostly from the point of view of the reaction of overcured stocks or secondary reaction products stemming from the original polysulfides. The reactions were carried out using the method described in a previous paper.


1983 ◽  
Vol 14 (40) ◽  
Author(s):  
A. V. ANISIMOV ◽  
T. A. KOLOSOVA ◽  
E. A. VIKTOROVA
Keyword(s):  

2018 ◽  
Vol 167 (2) ◽  
pp. 397-407 ◽  
Author(s):  
Jinning Suo ◽  
Cuili Zhang ◽  
Pin Wang ◽  
Liyan Hou ◽  
Qingshan Wang ◽  
...  

Author(s):  
Douglass Taber

Hervé Clavier and Steven P. Nolan, now at St. Andrew’s University, found (Adv. Synth. Cat. 2008, 350, 2959) that the indenylidene Ru complex 1 was an excellent pre-catalyst for alkene metathesis. A combination of 1 and the ligand 2 effected cross metathesis of 3 and 4 in just 15 minutes under microwave heating. Robert H. Grubbs of Caltech designed (Organic Lett. 2008, 10, 2693) the Ru catalyst 6 for the preparation of tri- and tetrasubstituted alkenes, as illustrated by the conversion of 7 to 8. The catalyst 6 also worked well for cross metathesis and ring opening metathesis polymerization (ROMP). For some biological applications, it would be desirable to run alkene cross metathesis under aqueous conditions. Benjamin G. Davis of the University of Oxford observed (J. Am. Chem. Soc. 2008, 130, 9642) that allyl sulfides such as 9 were unusually reactive in cross metathesis. Indeed, aqueous cross methathesis with such an allyl sulfide incorporated in a protein worked well, although added MgCl2 was required. The protein, a serine protease, maintained its activity after cross metathesis. α,β-Unsaturated thioesters such as 14 are excellent substrates for, inter alia, enantioselective Cu-catalyzed conjugate addition of Grignard reagents. Adriaan J. Minnaard and Ben L. Feringa of the University of Groningen found (J. Org. Chem. 2008, 73, 5651) that the thioacrylate 13 was an excellent substrate for cross methathesis, allowing ready preparation of 14 . Although alkene metathesis is often run in CH2Cl2 , benzene or toluene, these are not necessarily the optimal solvents. Siegfried Blechert of the TU Berlin established (Tetrahedron Lett. 2008, 49, 5968) that for the difficult cyclization of 16 to 17, hexafluorobenzene worked particularly well. The extended conformation (illustrated for 18) of an ester is more stable than the lactone conformation by about 5 kcal/mol. It is therefore not surprising that SonBinh T. Nguyen of Northwestern University observed (Organic Lett. 2008, 10, 5613) that attempted ring-closing metathesis of 18 gave only the dimer 20. On addition of the bulky Lewis acid 21, which can complex 18 in the lactone conformation, the reaction delivered the desired monomer 19. This should be a generally useful strategy for the cyclization of difficult ester substrates.


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