Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride: the effects of substituents on the cleavage of the cyclopropane ring

Author:

Kirihara Masayuki,Kakuda Hiroko,Tsunooka Makoto,Shimajiri Akihiro,Takuwa Tomofumi,Hatano Akihiko

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference16 articles.

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2. Specific ‘a’-bond cleavage: (a) Murai, S.; Aya, T.; Renge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974, 39, 858–859; (b) Rubottom G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097–2099; (c) Conia J. M.; Girard, C. Tetrahedron Lett. 1973, 14, 2767–2770; (d) Murai, S.; Seki, Y.; Sonoda, N. J. Chem. Soc. Chem. Commun. 1974, 1032–1033; (e) Ryu, I.; Matsumoto, K.; Ando, M.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1980, 21, 4283–4286; (f) Ryu, I.; Ando, M.; Ogawa, A.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1983, 105, 7192–7194; (g) Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330–12339; (h) Ryu, I.; Murai, S.; Sonoda, N. J. Org. Chem. 1986, 51, 2389–2391; (i) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296–3298; (j) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520–1521.

3. Specific ‘b’-bond cleavage: (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073–2074; (b) Lewicka-Piekut S.; Okamura, W. H. Synth. Commun. 1980, 10, 415–420; (c) Blanco, L.; Mansouri, A. Tetrahedron Lett. 1988, 29, 3239–3242; (d) Booker-Milburn, K. I. Synlett, 1992, 809–810; (e) Booker-Milburn K. I.; Thompson, D. F. Synlett 1993, 592–594; (f) Torii, S.; Okamoto T.; Ueno, N. J. Chem. Soc. Chem. Commun. 1978, 293–294; (g) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193–1196; (h) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545–548; (i) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819–827; (j) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691–1692.

4. The lead (IV) acetate oxidation of cyclopropane derivatives: a novel fragmentation reaction

5. Stereochemistry of the lead(IV) acetate fragmentation of 1-(trimethylsiloxy)bicyclo[n.1.0]alkanes

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