A new method for preparation of tetraalkyl orthocarbonates from sodium alkoxides, tetrachlorostannane, and carbon disulfide

Synthesis (Germany)

Volumn 1984, Issue 3, 1984, Pages 233-234

  Sakai, Shizuyoshi ^a   Kominami, Mitsuhiro ^a   Chonan, Kohzo ^a   Enomoto, Takayasu ^a   Fujinami, Tatsuo ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85077871848     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1984-30785     Document Type: Short Survey

References (8)

1. R. H. DeWolfe, Carboxylic Ortho Acid Derivatives, Academic Press, New York, 1970;.
2. R. H. DeWolfe ., Synthesis 1974, 153.
3. W. Kantlehner et al., Synthesis 1977, 73.
4. W. F. Bailey, M. Shih, J. Am. Chem. Soc. 104, 1769 (1982).
5. S. Sakai, Y. Kobayashi, Y. Ishii, J. Org. Chem. 36, 1176 (1971).
6. The hexamethoxystannate was prepared in situ from sodium me-thoxide and tetrachlorostannane, followed by the reaction with carbon disulfide to form only 4 (R = CHt). However, when Hj, CO-CS-SNa, prepared from sodium methoxide and carbon disulfide, was allowed to react with tetrachlorostannane, it gave (H3CO)2C=S, H3CO-C(S)-CH3, and 4 (R=CH?).
7. J. Lai, E. F. Devlin J. Polvm. Scl, Polym. Chem. Ed II, 119 (1973); C A, 78, 111822 (1973] reported that zinc dibutyl xanthate was thermolyzed in excess butanol to yield 43% of tetrabutyl orthocar-bonate. However, we could not obtained such a high yield of pure 4 (R~fl-C4H»).
8. Handbook of Chemistry and Physics, 52nd Edn., CRC Press, Cleveland, 1971-1972.