Bobbitt reaction
{{Short description|Chemical reaction}}
{{Reactionbox
| Name = Bobbitt reaction
| Type = Ring forming reaction
| NamedAfter = James M. Bobbitt
}}
The Bobbitt reaction is a name reaction in organic chemistry. It is named after the American chemist James M. Bobbitt.{{cite book|last1=Wang|first1=Zerong|title=Comprehensive organic name reactions and reagents|date=2009|publisher=John Wiley|location=Hoboken, N.J.|isbn=978-0-471-70450-8|pages=441–444}} The reaction allows the synthesis of 1-, 4-, and N-substituted 1,2,3,4-tetrahydroisoquinolines and also 1-, and 4-substituted isoquinolines.
General Reaction Scheme
The reaction scheme below shows the synthesis of 1,2,3,4-tetrahydroisoquinoline from benzaldehyde and 2,2-diethylethylamine.
Reaction Mechanism
A possible mechanism is depicted below:
File:Bobbitt Mechanismus V2.svg
First the benzaliminoacetal 3 is built by the condensation of benzaldehyde 1 and 2,2-diethylethylamine 2. After the condensation the C=N-double bond in 3 is hydrogenated to form 4. Subsequently, an ethanol is removed. Next, the compound 5 is built including the cyclization step. After that the C=C-double bond in 5 is hydrogenated . Thus, 1,2,3,4-tetrahydroisoquinoline 6 is formed.
Applications
The Bobbitt reaction has found application in the preparation of some alkaloids such as carnegine,{{cite journal | last1=Bobbitt |first1=James M. |last2=Roy |first2=Dibyendu Nath |last3=Marchand |first3=Anthony |last4=Allen |first4=Christopher Whitney |title=Synthesis of isoquinolines. VI. N-alkyl-1,2,4-tetrahydroisoquinolines |journal=J. Org. Chem. |volume=32 |issue=7 |year=1967 |pages=2225–2227 |doi=10.1021/jo01282a030}}. lophocerine, salsolidine, and salsoline.
See also
References
{{Reflist}}
{{DEFAULTSORT:Bobbitt reaction}}
Category:Nitrogen heterocycle forming reactions