A new route to polyselenoether macrocycles. Catalytic macrocyclization of 3,3-dimethylselenatane by [Re₂(CO)₉]

Abstract

3,3-Dimethylselenatane, S[upper bond 1 start]eCH₂CMe₂C[upper bond 1 end]H₂, DMSe is cyclooligomerized catalytically at 115 °C in the presence of [Re₂(CO)₉(S[upper bond 1 start]eCH₂CMe₂C [upper bond 1 end]H₂)] to yield three new polyselenoether macrocycles 3,3,7,7-tetramethyl-1,5-diselenacyclooctane, 3,3,7,7,11,11-hexamethyl-1,5,9-triselenacyclododecane, 3,3,7,7,11,11,15,15-octamethyl-1,5,9,13-tetra- selenacyclohexadecane and polymer of DMSe; all three macrocycles are characterized crystallographically; in all cases the gem-dimethyl groups are directed toward the exterior of the rings; interestingly, some methylene groups are directed to the interior.

References

1. (a) R. D. Adams and S. B. Falloon, Chem. Rev., 1995, 95, 2587; (b) J. Am. Chem. Soc., 1994, 116, 10 540; (c) R. D. Adams, J. E. Cortopassi and S. B. Falloon, Organometallics, 1995, 14, 1748; (d) R. D. Adams and S. B. Falloon, Organometallics, 1995, 14, 4594; (e) R. D. Adams, S. B. Falloon, J. Perrin, J. A. Queisser and J. H. Yamamoto, Chem. Ber., 1996, 126, 313; (f) R. D. Adams, J. A. Queisser and J. H. Yamamoto, Organometallics, 1996, 15, 2489.
2. S. R. Cooper, in Crown Compounds: Toward Future Applications, ed. S. R. Cooper, VCH, New York, 1992, ch. 15; S. R. Cooper and S. C. Rawle, Struct. Bonding (Berlin), 1990, 72, 1; A. J. Blake and M. Schröder, Adv. Inorg. Chem., 1990, 35, 1.
3. R. J. Batchelor, F. W. B. Einstein, I. D. Gay, J.-H. Gu, B. M. Pinto and X.-M. Zhou, J. Am. Chem. Soc., 1990, 112, 3706; R. J. Batchelor, F. W. B. Einstein, I. D. Gay, J.-H. Gu and B. M. Pinto, J. Organomet. Chem., 1991, 411, 147; W. Levason, J. J. Quirk and G. Reid, J. Chem. Soc., Dalton Trans., 1996, 3713; W. Levason, J. J. Quirk, G. Reid and C. S. Frampton, Inorg. Chem., 1994, 33, 6120; N. R. Champness, P. F. Kelly, W. Levason, G. Reid, A. M. Z. Slawin and D. J. Williams, Inorg. Chem., 1995, 34, 615.
4. (a) E. G. Hope and W. Levason, Coord. Chem. Rev., 1993, 122, 109; (b) I. Cordova-Reyes, E. VandenHoven, A. Mohammed and B. M. Pinto, Can. J. Chem., 1995, 73, 113; (c) R. J. Batchelor, F. W. B. Einstein, I. D. Gay, J.-H. Gu, B. D. Johnston and B. M. Pinto, J. Am. Chem. Soc., 1990, 112, 1297; (d) R. J. Batchelor, F. W. B. Einstein, I. D. Gay, J.-H. Gu, B. D. Johnston and B. M. Pinto, J. Am. Chem. Soc., 1989, 111, 6582; (e) B. M. Pinto, B. D. Johnston, R. J. Batchelor, F. W. B. Einstein and I. D. Gay, Can. J. Chem., 1988, 66, 2956; (f) B. M. Pinto, R. J. Batchelor, B. D. Johnston, F. W. B. Einstein and I. D. Gay, J. Am. Chem. Soc., 1988, 110, 2990.
5. H. J. Backer and F. S. Winter, Recl. Trav. Chim. Pays-Bas, 1937, 56, 492.
6. R. E. Wolf Jr., J. R. Hartman, J. M. E. Storey, B. M. Foxman and S. R. Cooper, J. Am. Chem. Soc., 1987, 109, 4328; J. M. Desper and S. H. Gellman, J. Am. Chem. Soc., 1990, 112, 6732; A. Y. Nazarenko, R. M. Izatt, J. D. Lamb, J. M. Desper, B. E. Matysik and S. H. Gellman, J. Am. Chem. Soc., 1990, 112, 6732; J. M. Desper and S. H. Gellman, J. Am. Chem. Soc., 1990, 112, 6732.
7. S. C. Rawle, G. A. Admans and S. R. Copper, J. Chem. Soc., Dalton Trans., 1988, 93.