1,3-Oxathiolane is an
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
with the formula . It is a saturated five-membered
heterocycle
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
with non-adjacent S and O atoms. It is the parent of numerous derivatives. The parent compound is of little practical value, but there is some
biotechnological interest in derivatives where one or more H atoms are replaced by other substituents.
Preparation and occurrence
:
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The compound is prepared by condensation of mercaptoethanol with formaldehyde, as typical for synthesis of thioacetals.
2-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of
passion fruit
''Passiflora edulis'', commonly known as passion fruit, is a vine species of passion flower native to the region of southern Brazil through Paraguay to northern Argentina. It is cultivated commercially in tropical and subtropical areas for its ...
and other fruits.
1,2-Oxathiolane
In contrast to the well-developed area of 1,3-oxathiolanes, 1,2-oxathiolane and its derivatives are not prevalent in the literature. The parent compound, which is derived from 3-mercaptopropanol, has been detected in solution
A bulky derivative has been characterized by
X-ray crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
.
[{{cite journal , doi=10.1021/ja00546a047 , title=Rearrangement of penicillin sulfoxides in base. Penicillin-derived sulfines , date=1980 , last1=Baldwin , first1=Jack E. , last2=Herchen , first2=Stephen R. , last3=Schulz , first3=Guenter , last4=Falshaw , first4=Christopher P. , last5=King , first5=Trevor J. , journal=Journal of the American Chemical Society , volume=102 , issue=26 , pages=7815–7816 ]
References
Oxathiolanes