SYNTHESIS OF VARIOUS IODYL COMPOUNDS OF IODOARENES AND TETRAZOLES USING OXONE AS AN OXIDANT
SYNTHESIS OF VARIOUS IODYL COMPOUNDS OF IODOARENES AND TETRAZOLES USING OXONE AS AN OXIDANT
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Date
2013-07-05
Authors
Dhakal, Ram Chandra
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Publisher
Middle Tennessee State University
Abstract
Iodyls are interesting compounds. To date, much of this interest has been focused on the application of iodyls as unique oxidants in organic synthesis. In this work, we are interested in their application as energetic materials.
When Oxone<super>®</super> was used as an oxidant in the preparation of iodyl compounds, more than 99% pure product based on NMR analysis was obtained without extra purification of the products. This method is also able to recover the unreacted starting material by washing the precipitate of iodyl compound with appropriate organic solvents.
Eleven iodyl compounds with good yields have been synthesized using Oxone<super>®</super>. After successfully establishing the reactions, the scales of some starting materials were increased up to 10 mmol. After increasing the reaction scales, the yields of the products did not decrease, indicating that this method is readily scalable. Due to the presence of two iodyl groups on the benzene ring, 1,4–diiodylbenzene was not soluble in DMSO. The melting points of the iodyl compounds are the decomposition points. <italic>p</italic>-Diiodylbenzene decomposed vigorously compared to the iodyl compounds having only one iodyl group, such as iodylbenzene, 2–iodylnitrobenzene, 3–iodylbenzonitrile, and 4–iodylbenzonitrile. From this observation, when the iodyl group on the benzene ring is more than one, the explosive character of the compounds increases. Iodyl compounds of the tetrazole derivatives, such as 5–(3–iodylphenyl)–1<italic>H</italic>-tetrazole and 5–(4–iodylphenyl)-1<italic>H</italic>-tetrazole, also decomposed vigorously at the corresponding decomposition points.
When Oxone<super>®</super> was used as an oxidant in the preparation of iodyl compounds, more than 99% pure product based on NMR analysis was obtained without extra purification of the products. This method is also able to recover the unreacted starting material by washing the precipitate of iodyl compound with appropriate organic solvents.
Eleven iodyl compounds with good yields have been synthesized using Oxone<super>®</super>. After successfully establishing the reactions, the scales of some starting materials were increased up to 10 mmol. After increasing the reaction scales, the yields of the products did not decrease, indicating that this method is readily scalable. Due to the presence of two iodyl groups on the benzene ring, 1,4–diiodylbenzene was not soluble in DMSO. The melting points of the iodyl compounds are the decomposition points. <italic>p</italic>-Diiodylbenzene decomposed vigorously compared to the iodyl compounds having only one iodyl group, such as iodylbenzene, 2–iodylnitrobenzene, 3–iodylbenzonitrile, and 4–iodylbenzonitrile. From this observation, when the iodyl group on the benzene ring is more than one, the explosive character of the compounds increases. Iodyl compounds of the tetrazole derivatives, such as 5–(3–iodylphenyl)–1<italic>H</italic>-tetrazole and 5–(4–iodylphenyl)-1<italic>H</italic>-tetrazole, also decomposed vigorously at the corresponding decomposition points.
Description
Keywords
Green Synthesis,
Iodyl Compounds,
Iodyl Compounds from Oxone,
Iodyl Compounds of Tetrazoles,
Potentially Explosive Compound,
Tetrazoles Derivatives