Synthesis of 4,5-dihydroazepine-3,6-dicarboxylate derivatives by stereoselective ring expansion-nucleophilic addition to 4-.alpha.-chloroalkyl-1,4-dihydropyridine-3,5-dicarboxylates

1984 ◽  
Vol 49 (20) ◽  
pp. 3871-3874 ◽  
Author(s):  
David A. Claremon ◽  
David E. McClure ◽  
James P. Springer ◽  
John J. Baldwin
Keyword(s):  
Nucleophilic Addition ◽  
Ring Expansion

Nucleophilic‐Addition‐Initiated Ring Expansion and Selectivity in Anionic Fragmentation

2018 ◽  
Vol 25 (8) ◽  
pp. 1842-1847 ◽  
Author(s):  
David Reyes Loya ◽  
Michaël De Paolis
Keyword(s):  
Nucleophilic Addition ◽  
Ring Expansion

Mn(i)-Catalyzed nucleophilic addition/ring expansion via C–H activation and C–C cleavage

2019 ◽  
Vol 55 (72) ◽  
pp. 10764-10767 ◽  
Author(s):  
Bingxian Liu ◽  
Yin Yuan ◽  
Panjie Hu ◽  
Guangfan Zheng ◽  
Dachang Bai ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Ring Expansion ◽  
Convenient Synthesis ◽  
Carbonyl Addition

The Mn(i)-Catalyzed C–H alkenylation/carbonyl addition/retro-Aldol cascade was realized leading to the convenient synthesis of seven- or eight-membered carbocycles.

scholarly journals Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

2020 ◽  
Vol 16 ◽  
pp. 515-523 ◽  
Author(s):  
Svetlana V Amosova ◽  
Andrey A Filippov ◽  
Nataliya A Makhaeva ◽  
Alexander I Albanov ◽  
Vladimir A Potapov
Keyword(s):  
Nucleophilic Substitution ◽  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Ring Expansion ◽  
Nucleophilic Attack ◽  
Substitution Reactions ◽  
Ring Contraction ◽  
Rearrangement Reaction ◽  
High Yields ◽  
Alkyl Propiolates

The reaction of 2-(bromomethyl)-1,3-thiaselenole with potassium selenocyanate proceeded via a rearrangement with ring expansion, leading to a six-membered 2,3-dihydro-1,4-thiaselenin-2-yl selenocyanate (kinetic product) which in turn underwent rearrangement with ring contraction to a 1,3-thiaselenol-2-ylmethyl selenocyanate (thermodynamic product). These rearrangements occurred by a nucleophilic attack of the selenocyanate anion at two different carbon atoms of the seleniranium intermediate. The efficient regioselective synthesis of alkyl, allyl, 2-propynyl, benzyl, 4-fluorobenzyl, and 2-pyridinylmethyl 1,3-thiaselenol-2-ylmethyl selenides was developed based on the generation of sodium 1,3-thiaselenol-2-ylmethylselenolate from 1,3-thiaselenol-2-ylmethyl selenocyanate or bis(1,3-thiaselenol-2-ylmethyl) diselenide followed by nucleophilic substitution reactions. Sodium 1,3-thiaselenol-2-ylmethylselenolate underwent nucleophilic addition to alkyl propiolates in a regio- and stereoselective manner affording 1,3-thiaselenol-2-ylmethyl vinyl selenides in high yields predominantly with Z-configuration. Not a single representative of the 1,3-thiaselenol-2-ylmethyl selenide scaffold has been previously described in the literature.

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