ChemInform Abstract: Aromatic Substituent Effect on the Stereoselectivity of the Gas-Phase Acid-Induced Ring Opening in 9,10-Oxides Derived from trans-1,2,3,4,4a, 10a-Hexahydrophenanthrene.

ChemInform ◽  
2010 ◽  
Vol 24 (45) ◽  
pp. no-no
Author(s):  
M. CHINI ◽  
P. CROTTI ◽  
F. MINUTOLO ◽  
E. DEZI ◽  
A. LOMBARDOZZI ◽  
...  
Keyword(s):  
Gas Phase ◽  
Substituent Effect ◽  
Ring Opening ◽  
Aromatic Substituent

Aromatic substituent effect on the stereoselectivity of the gas-phase acid-induced ring opening in 9,10-oxides derived from trans-1,2,3,4,4a,10a-hexahydrophenanthrene

Tetrahedron ◽  
1993 ◽  
Vol 49 (26) ◽  
pp. 5845-5858 ◽  
Author(s):  
Marco Chini ◽  
Paolo Crotti ◽  
Filippo Minutolo ◽  
Emanuela Dezi ◽  
Antonietta Lombardozzi ◽  
...  
Keyword(s):  
Gas Phase ◽  
Substituent Effect ◽  
Ring Opening ◽  
Aromatic Substituent

Thermal Addition Reaction of Aroylketene with Ethyl Vinyl Ether: Aromatic Substituent Effect on Aroylketene Reactivity

Heterocycles ◽  
1996 ◽  
Vol 43 (11) ◽  
pp. 2457 ◽  
Author(s):  
Takehiro Sano ◽  
Jun Toda ◽  
Toshiaki Saitoh ◽  
Taichi Oyama ◽  
Yoshie Horiguchi
Keyword(s):  
Vinyl Ether ◽  
Substituent Effect ◽  
Addition Reaction ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Aromatic Substituent ◽  
Thermal Addition

scholarly journals Formation of Highly Oxygenated Low-Volatility Products from Cresol Oxidation

2016 ◽  
Author(s):  
Rebecca H. Schwantes ◽  
Katherine A. Schilling ◽  
Renee C. McVay ◽  
Hanna Lignell ◽  
Matthew M. Coggon ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Gas Phase ◽  
Ring Opening ◽  
Chemical Ionization ◽  
First Generation ◽  
Direct Analysis ◽  
Organic Aerosol ◽  
Oxidation Products ◽  
Ionization Mass ◽  
Particle Phase

Abstract. Hydroxyl radical (OH) oxidation of toluene produces the ring-retaining products cresol and benzaldehyde, and the ring-opening products bicyclic intermediate compounds and epoxides. Here, first- and later-generation OH oxidation products from cresol and benzaldehyde are identified in laboratory chamber experiments. For benzaldehyde, first-generation ring-retaining products are identified, but later-generation products are not detected. For cresol, low-volatility (saturation mass concentration, C* ~ 3.5 × 104–7.7 × 10−3 μg m−3) first- and later-generation ring-retaining products are identified. Subsequent OH addition to the aromatic ring of o-cresol leads to compounds such as hydroxy, dihydroxy, and trihydroxy methyl benzoquinones and dihydroxy, trihydroxy, tetrahydroxy, and pentahydroxy toluenes. These products are detected in the gas phase by chemical ionization mass spectrometry (CIMS) and in the particle phase using offline direct analysis in real time mass spectrometry (DART-MS). Our data suggest that the yield of trihydroxy toluene from dihydroxy toluene is substantial. While an exact yield cannot be reported as authentic standards are unavailable, we find that a yield for trihydroxy toluene from dihydroxy toluene of ~ 0.7 (equal to the yield of dihydroxy toluene from o-cresol) is consistent with experimental results for o-cresol oxidation under low-NO conditions. These results suggest that even though the cresol pathway accounts for only ~ 20 % of the oxidation products of toluene, it is the source of a significant fraction (~ 20–40 %) of toluene secondary organic aerosol (SOA) due to the formation of low-volatility products.

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