Reactions of N-Methyl Cyclic Ketene-N,X-acetals (X = S, O) with Isocyanates and Isothiocyanate

Aihua Zhou; Liwei Cao; Haiqing Li; Zhuqing Liu; Charles U. Pittman Jr

doi:10.1055/s-2005-922792

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Synlett 2006(2): 201-206
DOI: 10.1055/s-2005-922792

LETTER

Reactions of N-Methyl Cyclic Ketene-N,X-acetals (X = S, O) with Isocyanates and Isothiocyanate

Aihua Zhou*, Liwei Cao, Haiqing Li, Zhuqing Liu, Charles U. Pittman Jr*
Department of Chemistry, Mississippi State University, Starkville, MS 39762, USA
Fax: +1(662)3257611; e-Mail: cpittman@ra.msstate.edu; e-Mail: zhou_aihua@yahoo.com;

Further Information

Publication History

Received 29 June 2005
Publication Date:
23 December 2005 (online)

Abstract
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Abstract

Nucleophilic N-methyl cyclic ketene-N,X-acetals (X = S, O) can react with electrophilic aryl isocyanates, vinyl isocyanates and aryl isothiocyanates to form mono-adducts, bis-adducts and spirobicyclic compounds.

Key words

N-methyl cyclic ketene-N,S-acetals - N-methyl cyclic ketene-N,O-acetals - aryl isocyanates - vinyl isocyanates - aryl isothiocyanate

References

1 Meyers AI. Nazarenko N. J. Am. Chem. Soc. 1972, 94: 3243

Crossref Google Scholar
2 Klemm E. Letsch J. J. Polym. Sci., Part A: Polym. Chem. 1994, 32: 2867

Crossref Google Scholar
3 Kurth MJ. Decker OH. Hakon H. Yanuck KD. J. Am. Chem. Soc. 1985, 107: 443

Crossref Google Scholar
4 Fukuda H. Oda M. Endo T. J. Polym. Sci., Part A: Polym. Chem. 1999, 37: 699

Crossref Google Scholar
5 McElvain SM. Degginger ER. Behun JD. J. Am. Chem. Soc. 1954, 76: 5736

Crossref Google Scholar
6 Wu Z. Stanley RR. Pittman CU. J. Org. Chem. 1999, 64: 8386

Crossref Google Scholar
7 Banville J. Grandmaison JL. Lang G. Can. J. Chem. 1974, 52: 80

Crossref Google Scholar
8 Daniel B. J. Org. Chem. 1979, 44: 1208

Crossref Google Scholar
9 Hayes R. Li K.-D. Leeming P. Wallace TW. Williams RC. Tetrahedron 1999, 55: 12907

Crossref Google Scholar
10 Wu Z. Cao L. Pittman CU. Recent Res. Dev. Polym. Sci. 1998, 2: 467

Google Scholar
11 Cao L. PhD Dissertation Mississippi State University; USA: 1998.

Google Scholar
12 Zhou AH. PhD Dissertation Mississippi State University; USA: 2004.

Google Scholar
13 Zhou AH. Pittman CU. Tetrahedron Lett. 2005, 46: 2045

Crossref Google Scholar
14 Zhou AH. Pittman CU. Tetrahedron Lett. 2004, 45: 8899

Crossref Google Scholar
15 Zhu PC. Lin J. Pittman CU. J. Org. Chem. 1995, 60: 5729

Crossref Google Scholar
16 Zhou AH. Pittman CU. Tetrahedron Lett. 2005, 46: 3801

Crossref Google Scholar
17 Fukuda H. Oda M. Endo T. J. Polym. Sci., Part A: Polym. Chem. 1999, 37: 699

Crossref Google Scholar
18 Fukuda H. Oda M. Endo T. Macromolecules 1996, 29: 3043

Crossref Google Scholar
19 Klemm E. Letsch J. J. Polym. Sci., Part A: Polym. Chem. 1994, 32: 2867

Crossref Google Scholar
20 Fukuda H. Oda M. Endo T. Macromol. Rapid Commun. 1998, 19: 149

Crossref Google Scholar
21 Li H. MSc Thesis Mississippi State University; USA: 2000.

Google Scholar
22 Liu Z. MSc Thesis Mississippi State University; USA: 2003.

Google Scholar
23 Fukuda H. Endo T. Tetrahedron Lett. 1988, 29: 2327

Crossref Google Scholar
24 Cimminiello G. Graziano ML. Synthesis 1989, 54

Article in Thieme Connect Google Scholar
25 Gilman JW. Otonari YA. Synth. Commun. 1993, 23: 335

Google Scholar
26 Rigby JH. Balasubramanian N. J. Org. Chem. 1984, 49: 4569

Crossref Google Scholar
27 Snider BB. Song FB. Org. Lett. 2000, 2: 407

Crossref Google Scholar
28 Rigby JH. Lee C. Org. Lett. 2003, 5: 1151

Crossref Google Scholar
29 Takahashi E. Mukaiyama T. Chem. Lett. 2005, 34: 216

Crossref Google Scholar
30 Elliott MC. Elbertus K. Chem. Commun. 1997, 23: 2311

Google Scholar
31 Inaba S.-I. Ojima I. Yoshida K. Nagai M. J. Organomet. Chem. 1979, 164: 123

Crossref Google Scholar