105500-35-4

Upstream product

• 1755-01-7 endo-Dicyclopentadien 
• 110793-48-1 exo-5-hydroperoxytricyclo(5.2.1.0.^2,6)deca-3,8-diene 
• 186581-53-3 diazomethane 
• 105469-25-8 1,4,7,7aα-tetrahydro-1-oxo-4α,7α-methano-3aH-indene-(3aR)-3aα-carboxylic acid 

Downstream Products

• 181219-02-3 (3S,3aR,4R,7S,7aR)-3-(3-Benzyloxy-1,1-dimethyl-propyl)-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one 
• 328583-84-2 (2R,5R)-2-tert-butyl-5-[(1S,2S,3R,6S,7R)-5-oxotricyclo[5.2.1.0^2,6]dec-8-en-3-yl]-5-phenyl-1,3-dioxolan-4-one 
• 51493-69-7 sordaricin 
• 181219-15-8 Benzoic acid (3S,3aS,3bS,6aS,7aS)-4,4,6a-trimethyl-decahydro-cyclopenta[a]pentalen-3-ylmethyl ester 
• 181219-13-6 Benzoic acid (3S,3aS,3bS,6aR,7R,7aR)-7-hydroxy-4,4,6a-trimethyl-decahydro-cyclopenta[a]pentalen-3-ylmethyl ester 
• 181219-12-5 Benzoic acid (3S,3aS,3bS,6aR,7R,7aR)-7-formyloxy-4,4,6a-trimethyl-decahydro-cyclopenta[a]pentalen-3-ylmethyl ester 
• 181219-14-7 Benzoic acid (3S,3aS,3bS,6aR,7R,7aR)-4,4,6a-trimethyl-7-methylsulfanylthiocarboxyoxy-decahydro-cyclopenta[a]pentalen-3-ylmethyl ester 
• 123848-90-8 (3S,3aS,4R,7S,7aR)-3-Methyl-3-p-tolyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one 
• 56-86-0 L-glutamic acid 
• 132316-96-2 (S)-N-benzyl-N-(benzyloxycarbonyl)glutamic acid 
• 159947-29-2 (1S,2S,3S,6S,7R)-3-benzylaminotricyclo<5.2.1.0^2,6>dec-8-ene 
• 159947-28-1 Benzyl-(3aS,4R,7S,7aR)-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-(1Z)-ylidene-amine 

Relevant academic research and scientific papers

3,4-EPOXY-5-HYDROXYCYCLOPENTENE VIA TITANIUM(IV)-CATALYZED PHOTOOXYGENATION AND ITS PYROLYSIS TO 2,4-PENTADIENOIC ACID.

The epoxy alcohol exo-6-hydroxy-exo-4-oxatetracyclo(6.2.1.0.2,703,5)-undec-9-ene (1a) was synthesized by photooxygenation of dicyclopentadiene in the presence of Ti(OiPr)4; vacuum flash pyrolysis (520 deg C) of 1a resulted in 3,4.epoxy-5-hydroxycyclopentene (2) as intermediate, wich at elevated temperature rearranged into the cis- and trans-2,4-pentadienoic acids (8).

Regioselective Oxidation of Carbon-Carbon Double Bond of endo-Dicyclopentadiene

endo-9-Oxatetracyclo2.6.08.10>undec-3-ene (2) has been selectively prepared by the oxidation of endo-dicyclopentadiene (1) with chromium trioxide in acetic acid.On the other hand oxidation of 1 by pyridinium chlorochromate furnishes a 1 : 1 mixture of α-chloroketones (3 and 4) in high yield.A plausible mechanism is advanced to explain the formation of 3 and 4.

Dicyclopentadiene Oxidation I. Uncatalyzed Liquid-Phase Oxidation of Dicyclopentadiene

Dicyclopentadiene is oxidized by molecular oxygen to a mixture of the monoepoxides 2 and 3.The identification of the epoxides 2, 3 and 4 was executed with authentic samples prepared by epoxidation with peracetic acid or with tert-butylhydroperoxide in the presence of MoO2(acac)2.The main product is the substituted norbornene oxide 2.Allylic oxidation is also observed.Remarkable amounts of hydroperoxides can be determined iodometrically.The formation of allylic oxidation products 7, 8, 9 and 10 was proved by GC-MS-analysis.It is shown that in the uncatalyzed liquid phase oxidation of dicyclopentadiene no more than 50 percent of epoxides are formed.The bisepoxide 4 was found in small amounts only at higher conversions of the dicyclopentadiene.