Thial

A thial or thioaldehyde is a functional group in organic chemistry which is similar to an aldehyde, RC(O)H, in which a sulfur (S) atom replaces the oxygen (O) atom of the aldehyde (R represents an alkyl or aryl group). Thioaldehydes are even more reactive than the thioketones. Unhindered thioaldehydes are generally unstable — for example, thioformaldehyde, H2C=S, condenses to the cyclic trimer 1,3,5-trithiane.[1] With sufficient steric bulk, however, stable thioaldehydes can be isolated.[2]

In early work, the existence of thioaldehydes was inferred by trapping processes. For instance the reaction of Fc2P2S4 with benzaldehyde was proposed to form thiobenzaldehyde, which forms a cycloadduct with the dithiophosphine ylides to form a C2PS3 ring.[3]

See also

References

  1. ^ H. W. Kroto, B. M. Landsberg, R. J. Suffolk, A. Vodden (1974). "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH3CHS, and thioacetone, (CH3)2CS". Chem. Phys. Lett. 29 (2): 265–269. Bibcode 1974CPL....29..265K. doi:10.1016/0009-2614(74)85029-3. 
  2. ^ N. Takeda, N. Tokitoh, R. Okazaki (1997). "Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes". Chem. Eur. J. 3: 62–69. doi:10.1002/chem.19970030111. 
  3. ^ A. Capperucci, A. Degl’Innocenti, P. Scafato, P. Spagnolo (1995). "Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes". Chemistry Letters 24 (2): 147. doi:10.1246/cl.1995.147.