Free radical chain reactions of [1.1.1]propellane with three-coordinate phosphorus molecules. Evidence for the high reactivity of the bicyclo[1.1.1]pent-1-yl radical

Journal of the American Chemical Society

Volumn 119, Issue 6, 1997, Pages 1388-1399

  Dockery, Kevin P ^a   Bentrude, Wesley G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030944545     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962287z     Document Type: Article

References (83)

1. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
2. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
3. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
4. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
5. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
6. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
7. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
8. For recent reviews on the chemistry of small ring propellanes and the formation of bridgehead free radicals, see: (a) Kaszynski, P.; Michl, J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, p 773. (b) Szeimies, G. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: Greenwich, 1992; Vol. 2, p 1. (c) Walton, J. C. Chem. Soc. Rev. 1992, 21, 104. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312. (d) Kaszynski, P.; Michl, J. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London: 1995; Vol. 4, p 283. (e) Tobe, Y. In Carbocylic Cage Compounds: Chemistry and Applications; Osawa, E., Yonemitsu, O., Eds.; VCH: New York, 1992; p 125. (f) Wiberg, K. B. Chem. Rev. 1989, 89, 975. (g) Ginsburg, D. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Vol. 1, p 1193.
9. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
10. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
11. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
12. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
13. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
14. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
15. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
16. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
17. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
18. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
19. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
20. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
21. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
22. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
23. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
24. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
25. For recent papers on the free radical chemistry of [1.1.1]propellane, see: (a) Scaiano, J. C.; McGarry, P. F. Tetrahedron Lett, 1993, 34, 1243. (b) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. (c) Obeng, Y. S.; Laing, M. E.; Friedli, A. C.; Yang, H. C.; Wang, D.; Thulstrup, E. W.; Bard, A. J.; Michl, J. J. Am. Chem. Soc. 1992, 114, 9943. (d) Kaszynski, P.; McMurdie, N. D.; Michl, J. J. Org. Chem. 1991, 56, 307. (e) Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194. (f) Sadovaya, N. K.; Blokhin, A. V.; Surmina, L. S.; Tyurekhodzhaeva, M. A.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 2451. (g) Sadovaya, N. K.; Blokhin, A. V.; Tyurekhodzhaeva, M. A.; Grishin, Yu.K.; Surmina, L. S.; Koz'min, A. S.; Zefirov, N. S. Izv. Akad. Nauk SSSR., Ser. Khim. 1990, 716. (h) Kaszynski, P.; Friedli, A. C.; McMurdie, N. D.; Michl, J. Mol. Cryst. Liq. Cryst. 1990, 191, 193. (i) Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl. J. J. Org. Chem. 1990, 55, 1013. (j) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1989, 111, 3750. (k) McGarry, P. F.; Johnston, L. J.; Scaiano, J. C. J. Org. Chem. 1989, 54, 6133. (l) Murthy, G. S.; Hassenrueck, K.; Lynch, V. M.; Michl, J. J. Am. Chem. Soc. 1989, 111, 7262. (m) Bunz, U.; Polborn, K.; Wagner, H.-U.; Szeimies, G. Chem. Ber. 1988, 121, 1785. (n) Kaszynski, P.; Michl, J. J. Am. Chem. Soc. 1988, 110, 5225. (o) Kaszynski, P.; Michl, J. J. Org. Chem. 1988, 53, 4593. (p) Zefirov, N. S.; Sadovaya, N. K.; Surmina, L. S.; Godunov, I. A.; Koz'min, A. S.; Potekhin, K. A.; Maleev, A. V.; Struchkov, Yu.T. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 2648. (q) Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553.
26. 6
27. Wiberg, K. B.; Walker, F. H. J. Am Chem. Soc. 1982, 104, 5239.
28. Feller, D.; Davidson, E. R. J. Am. Chem. Soc. 1987, 109, 4133.
29. Wiberg, K. B.; Hadad, C. M.; Sieber, S.; Schleyer, P. v. R. J. Am. Chem. Soc. 1992, 114, 5820.
30. A series of radicals, tertiary butoxy, phenylthiyl, triethylsilyl, benzene-complexed chlorine atom, and p-methoxybenzoyl add to [1.1.1]propellane (1) about 2-3 times more rapidly than they add to styrene. (Scaiano, J. C., private communication. Data given in ref 1a).
31. 9
32. Rhodes, C. J.; Walton, J. C.; Della, E. W. J. Chem. Soc., Perkin Trans. 2 1993, 2125.
33. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
34. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
35. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
36. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
37. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
38. For reviews of phosphoranyl radicals, see: (a) Bentrude, W. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Sussex, 1990; Vol. 1, p 531; (b) Bentrude, W. G. In Reactive Intermediates. Abramovitch, R. A., Ed.; Plenum: London, 1983; Vol. 3, p 199. (c) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117. (d) Roberts, B. P. In Advances in Free Radical Chemistry; Williams, G. H., Ed.; Heyden and Sons: London, 1980; Vol. 6, p 225. (e) Schipper, P.; Janzen, E. H. J. M.; Buck, H. M. Top. Phosphorus Chem. 1977, 9, 407. (f) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; p 595.
39. Bentrude, W. G.; Alley, W. D.; Johnson, N. A.; Murakami, M.; Nishikida, K.; Tan, H.-W. J. Am. Chem. Soc. 1977, 99, 4383.
40. (a) Fu, J.-J. L.; Bentrude, W. G. J. Am. Chem. Soc. 1972, 94, 7710.
41. (b) Fu, J.-J. L.; Bentrude, W. G.; Griffin, C. E. J. Am. Chem. Soc. 1972, 94, 7717.
42. (c) Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am. Chem. Soc. 1977, 99, 7589.
43. (d) Reference 11 and 12 are concerned with reactions of dimethylamino and phenyl radicals with trialkyl phosphites.
44. 10a of phenyl-substituted phosphoranyl radicals which may be of increased stability compared to their TBP σ radical counterparts.
45. Tables of first-order rate constants for reactions of radicals with three-coordinate phosphorus molecules are found in refs 10a-10d.
46. This sort of understanding of the reactions of radicals with three-coordinate phosphorus molecules, in terms of three reaction classes, was first set forth in refs 15 and 16.
47. Bentrude, W. G.; Hansen, E. R.; Khan, W. A.; Min, T. B.; Rogers, P. E. J. Am. Chem. Soc. 1973, 95, 2286. Bentrude, W. G.; Rogers, P. E. J. Am. Chem. Soc. 1976, 98, 1674.
48. Bentrude, W. G.; Hansen, E. R.; Khan, W. A.; Min, T. B.; Rogers, P. E. J. Am. Chem. Soc. 1973, 95, 2286. Bentrude, W. G.; Rogers, P. E. J. Am. Chem. Soc. 1976, 98, 1674.
49. Bentrude, W. G.; Fu, J.-J. L.; Rogers, P. E. J. Am. Chem. Soc. 1973, 95, 3625.
50. Davies, A. G.; Griller, D.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1972, 2224.
51. Preliminary studies of the reactions of alkyl radicals with trialkyl phosphites and alkylphosphonites were carried out in this laboratory by E. R. Hansen and P. E. Rogers. For a preliminary report of a portion of the results reported in the present paper, see: Dockery, K. P.; Bentrude, W. G. J. Am. Chem. Soc. 1994, 116, 10332.
52. The preparation and assignment of cis and trans geometries to 8 and its sulfides were reported previously from this group. Bentrude, W. G.; Tan, H.-W. J. Am. Chem. Soc. 1976, 98, 1850. Cis and trans designations refer to the relation of the ring methyl and alkyl substituent on phosphorus. The stereospecific conversion of three-coordinate phosphorus to the sulfide with retention of configuration is well established. (Young, D. P.; McEwen, W. E.; Velez, D. C.; Johnson, J. W.; Van-derWerf, C. A. Tetrahedron Lett. 1964, 359. Horner, L.; Winkler, H. Tetrahedron Lett. 1964, 175.)
53. The preparation and assignment of cis and trans geometries to 8 and its sulfides were reported previously from this group. Bentrude, W. G.; Tan, H.-W. J. Am. Chem. Soc. 1976, 98, 1850. Cis and trans designations refer to the relation of the ring methyl and alkyl substituent on phosphorus. The stereospecific conversion of three-coordinate phosphorus to the sulfide with retention of configuration is well established. (Young, D. P.; McEwen, W. E.; Velez, D. C.; Johnson, J. W.; Van-derWerf, C. A. Tetrahedron Lett. 1964, 359. Horner, L.; Winkler, H. Tetrahedron Lett. 1964, 175.)
54. The preparation and assignment of cis and trans geometries to 8 and its sulfides were reported previously from this group. Bentrude, W. G.; Tan, H.-W. J. Am. Chem. Soc. 1976, 98, 1850. Cis and trans designations refer to the relation of the ring methyl and alkyl substituent on phosphorus. The stereospecific conversion of three-coordinate phosphorus to the sulfide with retention of configuration is well established. (Young, D. P.; McEwen, W. E.; Velez, D. C.; Johnson, J. W.; Van-derWerf, C. A. Tetrahedron Lett. 1964, 359. Horner, L.; Winkler, H. Tetrahedron Lett. 1964, 175.)
55. 15
56. Unpublished results from this laboratory.
57. 12b
58. For earlier presentations of figures similar to Figure 1 that represent the potential reactions of free radicals with three-coordinate phosphorus molecules, including substitution, oxidation, and free-radical Arbuzov, see refs 10a,b,c,f, 15, and 16.
59. Tables of average bond strengths for these substituents are recorded in ref 10 a-c,f, and 16.
60. 2a,n
61. A somewhat higher average bond strength (and in our view an unreasonably high one) is calculated using a more recent heat of formation of the dimethylamino radical. Golden, D.; Solly, R. K.; Gac, N. A.; Benson, S. W. J. Am. Chem. Soc. 1972, 94, 363.
62. (a) Davies, A. G.; Maxwell, J. P.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1974, 973.
63. (b) Boekestein, G.; Jansen, E. H. J. M.; Buck, H. M. J. Chem. Soc., Chem. Commun. 1974, 118.
64. For selected papers on the geometries of unconstrained alkyl radicals, see: (a) Pacansky, J.; Koch, W.; Miller, M. D. J. Am. Chem. Soc. 1991, 113, 317 and references therein. (b) Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 5046.
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78. 31P NMR chemical shifts: Quin, L. D.; Gordon, M. D.; Lee, S. O. Org. Magn. Reson. 1974, 6, 503 and references therein.
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81. Use of Kimax filtered light avoids the photo-Arbuzov isomerization of benzyl phosphites studied in this laboratory. Omelanzcuk, J.; Sopchik, A. E.; Lee, S.-G.; Akutagawa, K.; Cairns, S. M.; Bentrude, W. G. J. Am. Chem. Soc. 1988, 110, 6908. Cairns, S. M.; Bentrude, W. G. Tetrahedron Lett. 1989, 30, 1025; Bentrude, W. G.; Mullah, K. B. J. Org. Chem. 1991, 56, 7218.
82. Use of Kimax filtered light avoids the photo-Arbuzov isomerization of benzyl phosphites studied in this laboratory. Omelanzcuk, J.; Sopchik, A. E.; Lee, S.-G.; Akutagawa, K.; Cairns, S. M.; Bentrude, W. G. J. Am. Chem. Soc. 1988, 110, 6908. Cairns, S. M.; Bentrude, W. G. Tetrahedron Lett. 1989, 30, 1025; Bentrude, W. G.; Mullah, K. B. J. Org. Chem. 1991, 56, 7218.
83. Use of Kimax filtered light avoids the photo-Arbuzov isomerization of benzyl phosphites studied in this laboratory. Omelanzcuk, J.; Sopchik, A. E.; Lee, S.-G.; Akutagawa, K.; Cairns, S. M.; Bentrude, W. G. J. Am. Chem. Soc. 1988, 110, 6908. Cairns, S. M.; Bentrude, W. G. Tetrahedron Lett. 1989, 30, 1025; Bentrude, W. G.; Mullah, K. B. J. Org. Chem. 1991, 56, 7218.