With MHI Lithium Aluminum Hydride u c v c i u p i i t c i u u i Τ Λ Γ n r i l i - 7 t n .„ jft l i t h i u m o h i m i n i i m

ιιυττ i v^ i i i i i v juoo ιυι ui.iiiA.iiig i i i i n u n i u i u i n i n u i n hydride broaden the application of this powerful, ether soluble, reducing agent beyond aldehyde, ketone, ester and nitrile reductions. By combining other reagents with lithium aluminum hydride, mixed hydride systems are achieved that can be used to increase selectivity. In some cases reactions take an entirely new course. In other cases stereospecific reductions occur. Here are a few example reactions which can be of great significance in the field of organic synthesis and especially for the synthesis of pharma­ceuticals and natural products:

LAH

Usual: RR' C - CHR" LAH >RRT0HCH2R" (Most substituted alcohol)

New: RR' €— NCHR" } A H > RR'CHCHOHR" (Least substituted alcohol) AICI3

«g5c-<3>..-!uua|5.-<£X^SB Η (97-100%

trans) OH

CH3

C H 3 ^ New: CH3 - C

C H 3 · ^ (In excess)

< T > 0

C H 3 -

Ι Δ Η CH3 ^

•<5x:

Usuai: RC6H4C0C6h'4R* —^—^RCôH^CHOHCeH^iv

New: RC6H4C0C6H4R' - i ^ R C 6 H 4 C H 2 C 6 H 4 R '

Usual: 0 - NH2C6H4COOH L A H > o - NH2C6H4CH20H

New: 0 - NH2C6H4CO0H -^Uo - NH2C6H4CH3 AIC13

Usual: CcH^OCHoCcHc LAH

UH ^no reaction

New: C6H50CH2C6H5 - _ t ^ U c 6 H 5 0 H 4- C6H5CH3 (Ether cleavage) CoCI2

MHI lithium aluminum hydride is easy and safe to use. Reac­tions are rapid, yet easily controlled in conventional equipment. Reductions can be carried out at room temperature and atmos­pheric pressure. MHI Technical service is available to help you with your applications of lithium aluminum hydride.

For c o m p l e t e i n f o r m a t i o n ; Ζ • If you have not already received your copy, write for · : MHI's new booklet, "Selective Reductions of Organic · : Compounds with Complex Metal Hydrides" by Mark N. : : Rerick, University of Notre Dame. ·

ΓΙΓΓΊ C H E M I C A L · H V D R I D E D I V I S I O N

^m_3Ietal Hydrides Incorporated [ 1 J P I O N E E R S IN H Y D R I D E C H E M I S T R Y

518 C O N G R E S S S T R E E T , B E V E R L Y , M A S S A C H U S E T T S

M A Y 18, 1 9 5 9 C & E N 5 1

NEEW SELECTIVITY