Specific 1,2-Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β-Ketonitriles

2014 ◽  
Vol 2014 (29) ◽  
pp. 6380-6384 ◽  
Author(s):  
Zhanhui Yang ◽  
Kwon-Il Son ◽  
Siqi Li ◽  
Bingnan Zhou ◽  
Jiaxi Xu
Keyword(s):  
Boron Trifluoride ◽  
Aromatic Aldehydes ◽  
Simple Synthesis ◽  
Hydride Shift ◽  
Catalyzed Reactions

The question of Friedel-Crafts transformylations. Acid-catalyzed reactions of aromatic aldehydes with arenes

1987 ◽  
Vol 52 (8) ◽  
pp. 1591-1599 ◽  
Author(s):  
Royston M. Roberts ◽  
Ahmed M. El-Khawaga ◽  
Kevin M. Sweeney ◽  
Maher F. El-Zohry
Keyword(s):  
Aromatic Aldehydes ◽  
Acid Catalyzed ◽  
Catalyzed Reactions

ChemInform Abstract: γ-Regioselectivity of Lithiated 2-Buten-4-olide Towards Aromatic Aldehydes: A Simple Synthesis of γ-Arylidenebutenolides.

ChemInform ◽  
2010 ◽  
Vol 29 (51) ◽  
pp. no-no ◽  
Author(s):  
M. POHMAKOTR ◽  
P. TUCHINDA ◽  
P. PREMKAISORN ◽  
V. REUTRAKUL
Keyword(s):  
Aromatic Aldehydes ◽  
Simple Synthesis

Acetolytic cleavage of 2β,19-Epoxy-5α-cholestane involving a 1,2-Hydride shift to C2

1977 ◽  
Vol 30 (10) ◽  
pp. 2249 ◽  
Author(s):  
RE Gall ◽  
J Taylor
Keyword(s):  
Acetic Anhydride ◽  
Boron Trifluoride ◽  
Shift Reagent ◽  
Deuterium Exchange ◽  
Paramagnetic Shift ◽  
Nucleophilic Attack ◽  
Rearrangement Product ◽  
Hydride Shift ◽  
Carbonium Ion

Acetolytic cleavage of 2β,19-epoxy-5α-cholestane (1a) with boron trifluoride and acetic anhydride followed by hydrolysis gave the 2α,19- diol (2b), the only rearrangement product the 1α,19-diol (3b) and a mixture of olefins (4b). Deuterium exchange studies and the use of a paramagnetic shift reagent have shown that the reaction leading to the rearranged diol(3b) is not concerted and appears to involve an intermediate carbonium ion since hydride shift from both C 1 and C 3 occur. The formation of the 1α,19-diol (3b) as the only rearranged product can be rationalized as nucleophilic attack on the acetoxonium ion (8).

γ-Regioselectivity of lithiated 2-buten-4-olide towards aromatic aldehydes: a simple synthesis of γ-arylidenebutenolides

Tetrahedron ◽  
1998 ◽  
Vol 54 (37) ◽  
pp. 11297-11304 ◽  
Author(s):  
Manat Pohmakotr ◽  
Patoomratana Tuchinda ◽  
Pornchai Premkaisorn ◽  
Vichai Reutrakul
Keyword(s):  
Aromatic Aldehydes ◽  
Simple Synthesis

Unusual boron trifluoride-catalyzed reactions of taxinine derivatives with α- and β-4(20)-epoxides

1999 ◽  
Vol 40 (11) ◽  
pp. 2149-2152 ◽  
Author(s):  
Hirokazu Hosoyama ◽  
Hideyuki Shigemori ◽  
Jun'ichi Kobayashi
Keyword(s):  
Boron Trifluoride ◽  
Catalyzed Reactions

Scandium triflate-catalyzed selective ring opening and rearrangement reaction of spiro-epoxyoxindole and carbonyl compounds

RSC Advances ◽  
2016 ◽  
Vol 6 (102) ◽  
pp. 100307-100311 ◽  
Author(s):  
Hui Jiang ◽  
Haohua Jie ◽  
Jian Li
Keyword(s):  
Carbonyl Compounds ◽  
Ring Opening ◽  
Aromatic Aldehydes ◽  
Selective Ring Opening ◽  
Rearrangement Reaction ◽  
Catalyzed Reactions

Scandium triflate-catalyzed reactions between spiro-epoxyoxindole and carbonyl compounds have been disclosed. Furthermore, an unprecedented rearrangement takes place to yield alkylidene oxindoles when aromatic aldehydes are used as carbonyl components.

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