Cyclopropanes Synthesized Easily - C&EN Global Enterprise (ACS

Nov 6, 2010 - Basically, the method is this: An unsubstituted methylene group adds to the olefin double bond in the presence of a zinc-copper couple...
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RESEARCH Here's α N e w Route to Cyclopropanes

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Cyclopropanes Synthesized Easily A l a r g e number of cyclopropanes can be made from their corresponding olefins; yields a r e good V^IIU.WK:

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simply a large n u m b e r of cy clopropanes from their corresponding olefins Howard K. Simmons and Ronald D. Smith ot Du P o n t s Expérimental Station in Wilmington. Del., have developed a general method for preparing c> clopropanes from olefins ( J.ACS, Oct. 5, page 5 3 2 3 ) . Older methods, such as the dia/.omethane method, produced complex mixtures of products; to get the compound h e wanted, t h e chemist often had to use a n involved separation procedure. • Divalent Carbon Used. Basically, the" method is this: An unsubstitutecl methylene group adds to the1 olefin double bond in the presence of a zinccopper couple. F o r example, cy clohexene. methylene iodide, a n d zinccopper couple are stirred at reflux in anhydrous ethyl ether for 4 8 hours. Simple distillation gives a 4 8 ' r yield of p u r e bicyclo[4.1.0]heptane. Many substituted olefins, including some with functional groups, give t h e corresponding cyclopropanes in yields ranging from 10 to 70\ MAO play a role in controlling blood pressure, and N H I researchers ,w e studying the blood pressure eih'cts of MAO inhihitors. O n e such drug luts been found— 1-pheny !-2-lu dra/iuopropane. or JB 516. It controls hvpertension, and produces n o side eilects such as hhirred \isioii. constipation, aiui sexual impotence.

Protein Synthesis Clocked Two Har\ arcl University scientists. Elizabeth Ann Kigner and Robert B. Loi t field. ha\ e timed t h e biosynthesis of a protein. The\ have found that a moleeule ol ferritin [ AM iroii-coiitaininii protein) is completed fi\e and a halt minutes after its synthesis begins in iat liver. This work is especially important in studying cell metabolism and the uncontrolled cell growth associated with cancer. Eigner and Loftfield used rats fed on a diet low in iron before thev started the experiment. Because of this diet, there was n o significant accumulation of ferritin in the rats' livers. T h e researchers then triggered the ferritin synthesis by injecting colloidal iron oxide into the rats. Then they injected amino acids (valine and leucine) labeled M ith carbon-14. They timed the ferritin synthesis using the rate of uptake of the radioactive compounds into the ferritin in t h e liver. They found that the labeled amino acids were incorporated into ferritin slowly a t first. T h e uptake gradually increased, a n d after six minutes the rate of incorporation equaled the rate of n e t svnrhesis.

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• Etisul, cl iethx Î d i t b i o l i s o p h t h a l a t e . is a n e w d r u g w h i c h max c u t t r e a t m e n t t i m e for l e p i o s x t a d i c a l h . Ύ. I*'. l ) a \ e \ t o l d tin 7 t h I n t e r n a t i o n a l C o n g r e s s o n L e p r o b g v in T o k \ ο "I he d r u g h a s n o s i d e ellects. c a n h e r u b b e d i n t o t h e skin. T r e a t m e n t t i m e s u s i n g t h e new d r u g can be c u t f r o m t h e p r e s e n t t w o \ e a r s ( m a x i m u m 1 to p e r h a p s as l i t t l e as three m o n t h s . T h e drug's diseased e s t r o \ i u g p o w e r is d u e t o its r e l e a s i n g c t h x l i n e r e a p t a n i n t h e b o d y a f t e r it is rubbed into the skin. Davey began clinical trials w i t h E t i s u l i n 1957 a t the Nigerian Leprosy Service Research Unit. I'zuakoli. Eastern Nigeria. Clin­ i c a l work is s t i l l u n d e r w a y . • Ultraviolet l a m p s that w i l l f i l l the a i r x\ ilh l a r g e q u a n t i t i e s of n e g a t i v e i o n s arc t h e f o c u s o f a t t e n t i o n of s o m e W e s t i n g h i -i.se s c i e n t i s t s . Researchers h a x e f o u n d t h a t w h e n t h e a i r is c h a r g e d w i t h positive i o n s , d i s c o m f o r t s s u c h i s asthma, f a t i g u e , d i z z i n e s s , a n d h e a d ­ a c h e become m o r e p r o n o u n c e d . These discomforts become milder when people b r e a t h e air filled xvith n e g a t i v e ions.

• A new w a y t o s t u d y w a v e s f r o m u n ­ d e r g r o u n d a t o m i c e x p l o s i o n s has b e e n f o u n d b y Cornell University scientist J. \ Y . D a l l y . H e s e n d s xvaxes f r o m a fast burning e x p l o s i v e t h r o u g h m e t h a n e r u b I KM·. T h e soft m a t e r i a l sloxxs t h e w a v e s c l o w n so t h e y c a n h e p h o t o ­ graphed by a s e m i - h i g h s p e e d c a m e r a a n d then s t u d i e d i n d e t a i l . T h e w a v e s travel t h r o u g h the rubber m o d e l i n a b o u t one three h u n d r e d t h s of a s e c o n d .