Vishnumurthy, Kodumuru and Row, Tayur N Guru and Venkatesana, Kailasam (1998) Unusual photodimerization of 7-fluoro-4-methylcoumarin and 6-fluoro-4-methylcoumarin in the solid state. In: Tetrahedron, 54 (37). pp. 11235-11246.
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Photodimerization of 7-fluoro-4-methylcoumarin 1 is topochemical while 6-fluoro-4-methylcoumarin 2 does not lead to the expected product based on the topochemical principles. Compound 1 yield an anti-MT photodimer with a lower dimer conversion while compound 2 results in a syn-HH photodimer. The packing features of 1, 2 and 2a (the photodimer of 2) have been unequivocally established by single crystal X-ray diffraction studies. The rationale for the significant lower dimer conversion in 1 is provided. The defect induced dimerization reaction in 2 as a function of temperature is analyzed which verifies that the reaction proceeds with an induction period. The details of the interactions involving fluorine are analyzed.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Elsevier Science.|
|Department/Centre:||Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Division of Chemical Sciences > Organic Chemistry
|Date Deposited:||15 Dec 2009 12:06|
|Last Modified:||19 Sep 2010 05:28|
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