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Corrected structure 3.
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user55119
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Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

edited body
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user55119
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Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Added red arrow to structure 6 and bracketed intermediate 7.
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user55119
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Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Species 1 is your seventh structure. The C=N=N atoms are linear and a long reach for the remaining nitrogen. Electrocyclization of 1 to 2 restores aromaticity. Nitrene species 3 allows for a 1,2-shift to an electron-deficient center with concommitant loss of strain in the 4-membered ring to produce 1H-benzo[d][1,2,3]triazole 4.

Cyclization of 5 $\rightarrow$ 6 and dehydration via 7 gets the job done. Perhaps @Mithoron knows something that I am not aware of.

Added 3 in text.
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user55119
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equilibrium arrows between 1 and 2.
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user55119
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Corrected charges on structure 4.
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user55119
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Added resonance arrow between 2 and 3.
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user55119
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Source Link
user55119
  • 17.5k
  • 5
  • 60
  • 96
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