Polyhomologation: Synthesis of novel polymethylene architectures by a living polymerization of dimethylsulfoxonium methylide

Angewandte Chemie - International Edition

Volumn 37, Issue 10, 1998, Pages 1391-1393

  Shea, Kenneth J ^a   Busch, Brett B ^a   Paz, Manuel M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Boron; Oligomers; Polymerizations; Sulfur; Ylides

Indexed keywords

EID: 0032486331     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980605)37:10<1391::AID-ANIE1391>3.0.CO;2-0     Document Type: Article

References (16)

1. K. J. Shea, H. D. Zhu, J. Walker, M. Paz, J. Greaves, J. Am. Chem. Soc. 1997, 119, 9049-9050.
2. K. J. Shea, J. R. Walker, H. D. Zhu, US-A 5,476,915, 1995 [Chem. Abstr. 1996, 124, 177244].
3. a) Compound 1 is prepared by the deprotonation of trimethylsulfoxonium chloride with NaH;
4. b) E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353-1365.
5. a) H. C. Brown, J. J. Katz, B. A. Carlson, J. Org. Chem. 1973, 38, 3968-3970;
6. b) H. C. Brown, B. A. Carlson, ibid. 1913, 38, 2472-2424.
7. Dichloromethyl methyl ether is highly toxic! Proper protocols should be observed for its use.
8. -1.
9. 2 = 0.99978.
10. -1.
11. The RI response to 6 was opposite to that for 10.
12. J. A. Sonderquist, M. R. Najafi, J. Org. Chem. 1986, 51, 1330.
13. GPC analysis revealed incompletely resolved product peaks.
14. 1H NMR signals of 9 and 10 showed the presence of a 1:1 mixture.
15. f values for TLC (toluene/hexane/EtOAc 8/2/1): 10: 0.5, 9: 0.1.
16. n = 972.01): C 82.78, H 13.92; found: C 82.78, H 13,90.