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Mechanism of oxidative dearomatisation with hypervalent iodine
Mechanism of arene side chain oxidation by permanganateOxidative chlorination mechanism (sulfide to sulfonyl chloride)Reaction of ethylacetoacetate with IodineMechanism for oxidative cleavage of tertiary alcohols by NaOClReaction mechanism for 7-hydroxy-4-methylcoumarin synthesis with an iodine catalystMechanism of toluene oxidation with CrO3Mechanism - Dialkyne boron complex + Iodine?What is the mechanism for the oxidative cleavage of diketones via permanganate under basic/hot conditions?Oxidative Addition - Really concerted?Mechanism with hypohalite in haloform reaction
$begingroup$
The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) diacetate (PIDA). Being a high-valent iodine species, it is used as an oxidising agent in organic chemistry. So clearly, there is some sort of oxidation taken place in this step, along with nucleophilic aromatic substitution involving an $ce MeOH$ molecule. However, I am quite uncertain as to what is the mechanism by which this step takes place.
organic-chemistry reaction-mechanism aromatic-compounds organic-oxidation
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
$endgroup$
add a comment |
$begingroup$
The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) diacetate (PIDA). Being a high-valent iodine species, it is used as an oxidising agent in organic chemistry. So clearly, there is some sort of oxidation taken place in this step, along with nucleophilic aromatic substitution involving an $ce MeOH$ molecule. However, I am quite uncertain as to what is the mechanism by which this step takes place.
organic-chemistry reaction-mechanism aromatic-compounds organic-oxidation
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
$endgroup$
add a comment |
$begingroup$
The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) diacetate (PIDA). Being a high-valent iodine species, it is used as an oxidising agent in organic chemistry. So clearly, there is some sort of oxidation taken place in this step, along with nucleophilic aromatic substitution involving an $ce MeOH$ molecule. However, I am quite uncertain as to what is the mechanism by which this step takes place.
organic-chemistry reaction-mechanism aromatic-compounds organic-oxidation
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
$endgroup$
The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) diacetate (PIDA). Being a high-valent iodine species, it is used as an oxidising agent in organic chemistry. So clearly, there is some sort of oxidation taken place in this step, along with nucleophilic aromatic substitution involving an $ce MeOH$ molecule. However, I am quite uncertain as to what is the mechanism by which this step takes place.
organic-chemistry reaction-mechanism aromatic-compounds organic-oxidation
organic-chemistry reaction-mechanism aromatic-compounds organic-oxidation
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
edited Apr 20 at 10:05
orthocresol♦
40.6k7117250
40.6k7117250
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
asked Apr 20 at 6:07
Tan Yong BoonTan Yong Boon
4,38311148
4,38311148
add a comment |
add a comment |
1 Answer
1
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votes
$begingroup$
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para rather than ortho; it probably depends on the exact substitution pattern as I have seen examples of both. A good reference for this is Zhdankin, Hypervalent Iodine Chemistry (2013).
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
$endgroup$
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
add a comment |
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1 Answer
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1 Answer
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active
oldest
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active
oldest
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active
oldest
votes
$begingroup$
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para rather than ortho; it probably depends on the exact substitution pattern as I have seen examples of both. A good reference for this is Zhdankin, Hypervalent Iodine Chemistry (2013).
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
$endgroup$
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
add a comment |
$begingroup$
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para rather than ortho; it probably depends on the exact substitution pattern as I have seen examples of both. A good reference for this is Zhdankin, Hypervalent Iodine Chemistry (2013).
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
$endgroup$
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
add a comment |
$begingroup$
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para rather than ortho; it probably depends on the exact substitution pattern as I have seen examples of both. A good reference for this is Zhdankin, Hypervalent Iodine Chemistry (2013).
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
$endgroup$
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para rather than ortho; it probably depends on the exact substitution pattern as I have seen examples of both. A good reference for this is Zhdankin, Hypervalent Iodine Chemistry (2013).
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
answered Apr 20 at 10:09
orthocresol♦orthocresol
40.6k7117250
40.6k7117250
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
add a comment |
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
1
1
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
$begingroup$
Perhaps, the preference for the position of substitution is due to the stronger inductive withdrawal of the methoxy substituent already attached at that position.
$endgroup$
– Tan Yong Boon
Apr 20 at 15:12
add a comment |
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