Sulfuric Acid → HCID 520366, compound

HRID 1283907Notes

Reaction equation

HRID 1283907 reaction equation
[CH2:1]1[CH2:10][CH:9]2[CH2:11][CH:5]3[CH2:6][CH2:7][CH:8]2[CH:3]([CH2:4]3)[CH2:2]1.C=CCCCC1CCC=CC=1.S(=O)(=O)(O)O>CCCCC>[CH2:6]1[CH:5]2[CH2:4][CH:3]3[CH2:8][CH:9]([CH2:11]2)[CH2:10][CH:1]([CH2:2]3)[CH2:7]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 511452Decahydro-1,6-methanonaphthalene4×HCID 21516862HCID 21516862, compound

Product 1

HCID 520366HCID 520366, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

4-Homoisotwistane (II) is a compound disclosed by Krantz et al (Chem., Commun., 1971, 1287 and J. Amer. Chem. Soc., 95, 5662 (1973)) in their report concerning the selectivity of the intermolecular Diels-Alder reaction of 1-penten-5-ylcyclohexadienes. However, the selectivity of 4-homoisotwistane (II) is very low in this reaction and the starting 1-penten-5-ylcyclohexadiene is not readily available or cannot easily be synthesized. Accordingly, from the industrial viewpoint, it is very disadvantageous to synthesize 4-homoisotwistane according to the process of Krantz et al. Majerski et al (Tetrahedron Letters, 4915 (1973)) succeeded in synthesizing 4-homoisotwistane (II) in a yield of about 20 percent by reacting homoadamant-4-ene or homoadamantan-4-ol with concentrated sulfuric acid and n-pentane. This process also is industrially disadvantageous because it is difficult to obtain the starting homoadamantane derivatives.

Workup

  1. customcannot easily be synthesized

Sources & evidence

ORD record
ord-1502ef2be4a5425b861e072ad1de2fe0
Source dataset
uspto-grants-1976_08
Patent number
US03976710

Reaction notes

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