ChemInform Abstract: Ring Closure Reaction of 4-tert-Butyl-4-penten-1-ol with Electrophilic Reagents.

ChemInform ◽  
2010 ◽  
Vol 30 (28) ◽  
pp. no-no
Author(s):  
M. Lj. Mihailovic ◽  
S. Gojkovic ◽  
S Milosavljevic ◽  
S. Konstantinovic
1981 ◽  
Vol 36 (2) ◽  
pp. 266-267 ◽  
Author(s):  
Marianne Baudler ◽  
Jochen Hellmann
Keyword(s):  

Abstract Tri-tert-butyl-cyclotriphosphane is obtained by the dehalogenation of 1,3-diiodo-1,2,3-tri-tert-butyl-triphosphane with lithiumhydride. This reaction represents a so far unknown type of ring-closure leading to cyclotriphosphanes, which corresponds to the classical synthesis of cyclopropanes starting from 1,3-dichloropropanes.


1987 ◽  
Vol 52 (5) ◽  
pp. 1305-1314 ◽  
Author(s):  
Stanislav Böhm ◽  
Renata Prantová ◽  
David Šaman ◽  
Petr Trška ◽  
Josef Kuthan

The title compound IV reacted with sodium borohydride to give the 4H-pyran VIIa and the dienone VIIIa whereas its reaction with sodium cyanide afforded exclusively the dienone VIIIb. Reaction of the salt IV with tert-butylmagnesium chloride or bromide gave a mixture of the 4H-pyran VIIa and the corresponding 4-tert-butyl derivative V. Upon treatment with hydrogen sulfide and hydrogen chloride, this mixture afforded 2,4,6-tri-tert-butyl-4H-thiopyran XI whereas aromatization with chloranil and subsequent reaction with ammonium acetate resulted in 2,4,6-tri-tert-butylpyridine (X). Analogously, the perchlorate IV reacted with ammonium acetate to give 2,6-di-tert-butylpyridine (VI). Addition of triphenylphosphine and potassium phthalimide to IV afforded exclusively the 4H-pyran derivatives XII and XIII. A similar reaction of nitromethyl anion led to the 4,4'-bis(4H-pyran) derivative XIV. Mechanism of the studied reactions and the reasons for the low reactivity of the sterically hindered pyridine derivative VI with electrophilic reagents are discussed.


2006 ◽  
Vol 76 (9) ◽  
pp. 1397-1400 ◽  
Author(s):  
L. K. Sal’keeva ◽  
M. T. Nurmaganbetova ◽  
E. V. Minaeva ◽  
B. Z. Kokzhalova

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 564-572
Author(s):  
Richard Bunce ◽  
Field Watts

A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- and 2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure affords the final lactam products. The reactions proceed cleanly and only two chromatographic purifications are required.


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