A model for olefin hydration: intramolecular nucleophilic addition of phenolate oxygen to the unactivated double bond

1984 ◽  
pp. 1259 ◽  
Author(s):  
Christopher M. Evans ◽  
Anthony J. Kirby
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition

Nucleophilic Addition of the Double Bond of 2,4,6-Trinitrostyrene and Transformations of Adducts.

ChemInform ◽  
2006 ◽  
Vol 37 (18) ◽  
Author(s):  
O. Yu. Sapozhnikov ◽  
V. V. Mezhnev ◽  
M. D. Dutov ◽  
S. A. Shevelev
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition

The synthesis of 8-Azabenzo[4,5]cyclohepta[1,2,3-de]naphthalene: A new heterocyclic aromatic system

1971 ◽  
Vol 24 (4) ◽  
pp. 835 ◽  
Author(s):  
JT Craig ◽  
AD Woolhouse
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition ◽  
Theoretical Study ◽  
Aromatic System ◽  
Nitrogen Double Bond

8-Azabenzo[4,5]cyclohepta[1,2,3-de]naphthalene, a nitrogen analogue of one of the hypothetical hydrocarbons on which Pullman et al.1 have made a theoretical-study, has been synthesized. This compound has been found to undergo nucleophilic addition of water, methanol, or aniline to the carbon-nitrogen double bond with surprising ease, and a possible explanation for these reactions has been proposed.

meso-Tetraphenylporphyrin-derived oxypyriporphyrin, oxypyrichlorin, and thiomorpholinochlorin, as their Ni(II) complexes

2012 ◽  
Vol 16 (05n06) ◽  
pp. 576-588 ◽  
Author(s):  
Subhadeep Banerjee ◽  
Matthias Zeller ◽  
Christian Brückner
Keyword(s):  
Double Bond ◽  
Single Crystal ◽  
Nucleophilic Addition ◽  
Nickel Complex ◽  
Aldol Condensation ◽  
Trans Configuration ◽  
Free Base ◽  
X Ray ◽  
Methylene Groups ◽  
Lawesson's Reagent

trans-Diolchlorin was prepared by nucleophilic addition of methyl-Grignard bromide to meso-tetraphenyl-2,3-dioxoporphyrin, as its free base or Ni(II) complex. The trans-configuration of the vic-diol functionality was shown by single crystal X-ray diffractometry. The nickel complex of the trans-dimethyldiol proved susceptible to Pb(IV) acetate-induced, oxidative diol cleavage, generating a meso-tetraphenylsecochlorin bismethylketone Ni(II) complex, the first example of this chromophore class. Under Brønsted-basic conditions, this bisketone cyclized via an intramolecular aldol condensation to provide a meso-tetraphenyloxypyriporphyrin. Reduction of this porphyrin analog saturated the double bond in the pyridinone moiety, generating an oxypyrichlorin. Reaction of the meso-tetraphenylsecochlorin bismethylketone Ni(II) complex with Lawesson's reagent induced the formation of a thiomorpholinochlorin substituted with two methylene groups, the first example of any porphyrin analog containing a thiomorpholine moiety.

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