Radical-chain cyclisation of unsaturated acetals and thioacetals in the presence of thiols as polarity-reversal catalysts

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8929-8933

  Dang, Hai Shan ^a   Roberts, Brian P ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Catalysis; Cyclisation; Radical reactions; Radicals; Thiols

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 1,3 DITHIANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; ACETAL DERIVATIVE; RADICAL; SPIRO COMPOUND; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION;

EID: 0033544792     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01898-5     Document Type: Article

References (18)

1. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991. Nájera, C.; Yus, M. Org. Prep. Proced. Int.1995, 27, 383.
2. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991. Nájera, C.; Yus, M. Org. Prep. Proced. Int. 1995, 27, 383.
3. Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Venturini, A.; Zavitsas, A. A. Chem. Eur. J. 1997, 3, 376.
4. Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051.
5. Stien, D.; Samy, R.; Nouguier, R.; Crich, D.; Bertrand, M. P. J. Org. Chem. 1997, 62, 275.
6. Stein, D.; Crich, D.; Bertrand, M. P. Tetrahedron 1998, 54, 10779.
7. Bogen, S.; Journet, M.; Malacria, M. Synlett 1994, 958.
8. Nishida, A.; Nishida, M.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 7035.
9. Dang, H.-S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1998, 67.
10. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
11. 3 (b.p. 98-100°C at 0.04 mmHg) was prepared by treatment of the sodium salt of dimethyl malonate with 2-bromomethyl-1,3-dioxolane in DMF-benzene at 80°C for 16 h, followed by alkylation of the sodium salt of the malonate product with allyl bromide.
12. Obtained from Peroxid-Chemie and handled as a 50% w/w solution in involatile aliphatic hydrocarbons. The half-life of this peroxide is ca. 1 h at 125°C.
13. Herman, A.; Becker, B.; Wojnowski, W. Z. Anorg. Allg. Chem. 1979, 450, 178.
14. C (125.8 MHz) 12.1, 38.8, 40.2, 42.8, 52.8, 52.9, 55.6, 64.8, 65.2, 116.1, 172.1, 172.6. (Incomplete NMR data for this compound were given in Ref. 3). In reactions where the thiol and initiator were added twice, 5 mol% of each was present initially and the second 5 mol% portion of each was added after 40 min; the total reaction time was extended to 2.5 h.
15. Biddles, I.; Hudson, A.; Wiffen, J. T. Tetrahedron 1972, 28, 867. Griller, D.; Nonhebel, D. C.; Walton, J. C. J. Chem. Soc.,Perkin Trans. 2 1984, 1817.
16. Biddles, I.; Hudson, A.; Wiffen, J. T. Tetrahedron 1972, 28, 867. Griller, D.; Nonhebel, D. C.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1984, 1817.
17. Cai, Y.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1998, 467.
18. C 22.2, 22.6, 24.0, 24.2, 43.1, 43.5, 44.2, 52.4, 52.7, 60.9, 63.9, 65.0, 117.0, 170.4, 172.2. Satisfactory spectroscopic data and elemental analyses were obtained for all new compounds reported herein.