ChemInform Abstract: REACTIONS OF LITHIUM ALUMINUM HYDRIDE OR ALANE WITH OLEFINS CATALYZED BY TITANIUM TETRACHLORIDE OR ZIRCONIUM TETRACHLORIDE. A CONVENIENT ROUTE TO ALKANES, 1-HALOALKANES AND TERMINAL ALCOHOLS FROM ALKENES

1978 ◽  
Vol 9 (13) ◽  
Author(s):  
F. SATO ◽  
S. SATO ◽  
H. KODAMA ◽  
M. SATO
Keyword(s):  
Titanium Tetrachloride ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Zirconium Tetrachloride ◽  
Convenient Route

ANTINEOPLASTIC AGENTS: XI. N-BIS(2-BROMOETHYL)AMINES

1964 ◽  
Vol 42 (7) ◽  
pp. 1699-1706 ◽  
Author(s):  
George R. Pettit ◽  
Maurice R. Chamberland ◽  
David S. Blonda ◽  
Martyn A. Vickers
Keyword(s):  
Exchange Reaction ◽  
Antineoplastic Agents ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Efficient Synthesis ◽  
Nitrogen Mustards ◽  
Hydride Reduction ◽  
Halogen Exchange ◽  
Convenient Route

A novel halogen exchange reaction was found to accompany condensation of an acyl chloride with N-bis(2-bromoethyl)amine. Reaction between an acyl bromide and N-bis(2-bromoethyl)amine, however, gave the expected N-bis(2-bromoethyl)amide. A number of N-alkyl-N-bis(2-bromoethyl)amines were prepared by lithium aluminum hydride reduction of the corresponding N-bis(2-bromoethyl)amides. The overall transformation from N-bis(2-bromoethyl)amine presents a convenient route to certain bromo nitrogen mustards. An efficient synthesis of N-bis(2-iodoethyl)amine hydroiodide is also described.

ANTINEOPLASTIC AGENTS: X. N-BIS(2-FLUOROETHYL)AMINES

1964 ◽  
Vol 42 (3) ◽  
pp. 572-578 ◽  
Author(s):  
George R. Pettit ◽  
Robert L. Smith
Keyword(s):  
Aluminum Chloride ◽  
Antineoplastic Agents ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Potassium Fluoride ◽  
Lithium Aluminum ◽  
Nitrogen Mustards ◽  
Convenient Route

Successive conversion of N-bis(2-hydroxyethyl)-p-toluenesulphonamide (Ib) to respective dimethanesulphonate and difluoro derivatives (IIa, IIIa, and IIIc) was found to provide a convenient route to N-bis(2-fluoroethyl)amine. Reaction of N-bis(2-methanesulphonyl-oxyethyl)-p-toluenesulphonamide (IIIa) with limited quantities of potassium fluoride, in several pro tic solvents, was shown to yield N-(p-toluenesulphonyl)morpholine (IV). Utility of N-bis(2-fluoroethyl)amine as a precursor of fluoro-nitrogen mustards was illustrated by synthesis of two N-bis(2-fluoroethyl)benzylamines (IXb and Xa). Application of an aluminum chloride – lithium aluminum hydride reagent for hydrogenolysis of carbon–fluorine bonds was also suggested.

Preparation of Precocene 2 and 3,4-Epoxyprecocene 2 Deuterated Analogues at C-3, C-4 and C-3, C-4

1985 ◽  
Vol 40 (4) ◽  
pp. 556-558 ◽  
Author(s):  
F. Camps ◽  
A. Conchillo ◽  
A. Messeguer
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Deuterated Analogue ◽  
Convenient Route ◽  
Derivatives Of

A convenient route for the preparation of title compounds from benzopyran-4-one (1) and its corresponding 3,3-2H2 deuterated analogue (2) is reported. Treatment of 1 or 2 with lithium aluminum deuteride followed by dehydration afforded, respectively, 4-2H precocene (3c) or 3,4-2H2 precocene (3b). Likewise, reduction of 2 with lithium aluminum hydride and subsequent dehydration led to the formation of 3-2H precocene (3d). Finally, the corresponding 3,4-epoxy derivatives of all these compounds were prepared in good yields by conventional procedures.

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