CHLOROTHEXYLBORANE-METHYL SULFIDE COMPLEX)

Preparation

The most conveniently prepared Chloro(thexyl)borane-Dimethyl Sulfide is from commercially available monochloroborane-dimethyl sulfide complex and 2,3-dimethyl-2-butene in CH2Cl2 (eq 1).

Reactivity Profile

Chloro(thexyl)borane-Dimethyl Sulfide has very reactive with oxygen and moisture and must be handled using standard techniques for handling air-sensitive materials. Reported to be stable for at least two months when stored at 0 °C in CH2Cl2 solution under N2. It is reacts rapidly with protic solvents.

References

1. (a) Brown, H. C.; Sikorski, J. A.; Kulkarni, S. U.; Lee, H. D. JOC 1980, 45, 4540. (b) Brown, H. C.; Sikorski, J. A.; Kulkarni, S. U.; Lee, H. D. JOC 1982, 47, 863. (c) Sikorski, J. A.; Brown, H. C. JOC 1982, 47, 872. (d) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic: London, 1988.
2. (a) Brown, H. C.; Cha, J. S.; Yoon, N. M.; Nazer, B. JOC 1987, 52, 5400. (b) Brown, H. C.; Nazer, B.; Cha, J. S.; Sikorski, J. A. JOC 1986, 51, 5264. (c) Brown, H. C.; Cha, J. S.; Nazer, B.; Yoon, N. M. JACS 1984, 106, 8001.
3. Brown, H. C.; Sikorski, J. A. OM 1982, 1, 28.