Methylene blue cation → Anthracene

HRID 436243

Reaction equation

HRID 436243 reaction equation
C1C(I)=C(O)C(I)=C2OC3C([C:17]4(O[C:28](=O)[C:19]5[C:20](Cl)=[C:21](Cl)[C:22](Cl)=[C:23](Cl)[C:18]4=5)C=12)=CC(I)=C(O)C=3I.CN([C:37]1[CH:38]=[CH:39][C:40]2N=C3C(=CC(C=C3)=[N+](C)C)S[C:41]=2[CH:42]=1)C>>[CH:20]1[C:19]2[C:18](=[CH:17][C:37]3[C:38]([CH:28]=2)=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 4139Methylene blue cationHCID 69439Rose Bengal Lactone

Product 1

HCID 8418Anthracene

Procedure

(8.3 mmol) and 500 mg. of photosensitizing resin were mixed in 100 ml. of chloroform and irradiated. After 148 cc. (6.6 mmol) of oxygen was absorbed the resin was filtered off, the solution was decolorised with charcoal and evaporated to dryness. The residue was fractionally recrystallized from chloroform to yield anthracene endoperoxide, mp 137°-143°. Rose bengal attached to IRA-400 and methylene blue attached to IRC-200 both gave the same results.

Workup

  1. customboth gave the same results

Sources & evidence

ORD record
ord-8450af46488242d799e4407a346031bb
Source dataset
uspto-grants-1977_02
Patent number
US04008136

Linked notes

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