A likely intermediate during the CO2-induced activation of 2-alkylindoles toward electrophilic substitution: Structure of a unique tetramer formed by joining two boat-shaped (LiOCO)2 rings

Organometallics

Volumn 15, Issue 21, 1996, Pages 4355-4356

  Davies, Robert P ^a   Raithby, Paul R ^a   Snaith, Ronald ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039140832     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960739a     Document Type: Article

References (20)

1. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
2. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
3. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
4. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
5. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
6. For reviews, see for example: (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-541. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167-209. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47-142. (e) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501-1523. (f) Sapse, A. M., Schleyer, P. v. R., Eds. Lithium Chemistry: A Theoretical and Experimental Overview; John Wiley & Sons: New York, 1995.
7. For reviews, see for example: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988. (b) Brandsma, L. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Vol. 2. (c) Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1990; Vol. 15. (d) Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1. (e) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, FL,
8. For reviews, see for example: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988. (b) Brandsma, L. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Vol. 2. (c) Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1990; Vol. 15. (d) Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1. (e) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, FL,
9. For reviews, see for example: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988. (b) Brandsma, L. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Vol. 2. (c) Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1990; Vol. 15. (d) Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1. (e) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, FL,
10. For reviews, see for example: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988. (b) Brandsma, L. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Vol. 2. (c) Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1990; Vol. 15. (d) Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1. (e) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, FL,
11. For reviews, see for example: (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988. (b) Brandsma, L. Preparative Polar Organometallic Chemistry; Springer-Verlag: Berlin, 1990; Vol. 2. (c) Fieser, M. Reagents for Organic Synthesis; Wiley-Interscience: New York, 1990; Vol. 15. (d) Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1. (e) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, FL,
12. (a) Ball, S. C.; Cragg-Hine, I.; Davidson, M. G.; Davies, R. P.; Edwards, A. J.; Lopez-Solera, I.; Raithby, P. R.; Snaith, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 921-923.
13. (b) Ball, S. C.; Cragg-Hine, I.; Davidson, M. G.; Davies, R. P.; Raithby, P. R.; Snaith, R. J. Chem. Soc., Chem. Commun. 1996, 1581-1582.
14. Katritzky, A. R.; Akutagawa, K. J. Am. Chem. Soc. 1986, 108, 6808-6809.
15. 3: C, 67.42; H, 6.74; N, 5.24. Found: C, 66.82; H, 6.81; N, 5.25. Further characterization data are given in the Supporting Information.
16. 2 = 0.1216 on all data. All calculations were performed on a Viglen 486 PC using SHELXTL-PLUS and SHELXL93 software. Atomic coordinates, bond lengths and angles, and vibrational parameters have been deposited at the Cambridge Crystallographic Data Centre.
17. (a) Smith, G.; O'Relliy, E. J.; Kennard, C. H. L. Acta Crystallogr., Sect. C. 1986, 42, 1329-1331.
18. (b) Küppers, H. Ibid. 1988, 44, 2093-2095.
19. (c) Chen, X.-M.; Mak, T. C. W. J. Crystallogr. Spectrosc. Res. 1993, 23, 291.
20. The sum of the van der Waal's radii of C and O is ca. 3.20 Å. In hydrogen-bonded systems involving CH⋯O units, a short C⋯O distance, taken to imply a significant interaction, is in the range 3.0-3.5 Å.