Undecane 1-bromo

Gas chromatographic examination of another reaction mixture run on a 10-mmol scale with undecane as an internal standard indicates that 2-methyl-4 -nitrobipheny1 is formed in 90% yield based on l-bromo-4-nitrobenzene. The product obtained by this procedure shows the following properties mp 99-101 C (lit., mp 103-105°C) IR (neat) cm l 1600 (s), 1510 (s), 1480 (s), 1340 (s),... 

In order to testify to the versatility of the Reformatsky reaction, two examples of three-component processes are presented the synthesis of 3-aryl-4,4-dimethyl-2-oxaspiro[5.5] undecane-1,5-diones 1485 (equation 12), and the coupling of two molecules of methyl 2-bromo-2-methyl propanoate (If) with an oxoaryl acetaldehyde 15 to afford 3a-aryl-3,3,6,6-tetramethyl-tetrahydrofuro[3,2-b]furan-2,5-dione 1686 (equation 13). 

The tricyclic compound 3-methoxytricyclo[5.4.0.02-8]undecan-9-one (21) was conveniently prepared in 91 % yield by treating 2-bromo-3-methoxybicyclo[5.4.0]undecan-9-one with sodium hydride in dimethyl sulfoxide.20... 

The intermolecular Diels-Alder reaction between the dibromoenone (111) and dienes (112) provides access to bicyclo[5.4.0]undecane systems (113) that are common core structures of many natural products (Scheme 32).118 The alio-threonine-derived O-(/ -biphenyl carbonyl oxy)-/i-phenyloxazaborolidi none catalyses the enan-tioselective Diels-Alder reaction of acyclic enones with dienes.119 The reversal of facial selectivity in the Diels-Alder cycloaddition of a semicyclic diene with a bro-moenone was induced by the presence of the bromo substituent in the dienophile.120 Mixed Lewis acid catalyst (AlBr3/AIMe3) catalyses the Diels-Alder reaction of hindered silyloxydienes with substituted enones to produce highly substituted cyclohexenes.121 Chiral /V-enoyl sultams have been used as chiral auxiliaries in the asymmetric Diels-Alder reactions with cyclopentadiene.122... 

With diethyl ether as solvent, the reaction proceeds with the selective reduction of the tosyl group to give 1-bromo-n-undecane, whereas in diethylene glycol dimethyl ether ( digl5Tne ), the bromo substituent is selectively reduced to yield n-undecyl tosylate. In diethyl ether, the lithium cation is poorly solvated and LiAlIEt reacts as an ion pair. In... 

High molecular-weight aliphatic aldehydes have been made by the dis tillation of a-hydroxy acids, which are prepared by the hydrolysis of the corresponding a-bromo acids. The reaction is carried out under diminished pressure or in an atmosphere of carbon dioxide. Details for the procedure are found in the preparation of octanal (57%) and undecanal (96%). Preparation of the a-bromo acid and its subsequent hydrolysis are also described. A later modification has been the distillation of the a-methoxy acid in the presence of copper. This procedure gives an almost quantitative yield in the preparation of heptadecanal. ... 

Thus, reaction of humulene (1) with A -bromosuccinimide in aqueous acetone, or with hypobromous acid, gave a 1 1 mixture of 9-bromo-l,4,4-trimethyl-8-methylenecycloundeca-l,5-diene (2) and 5-bromo-8-hydroxy-4,8,ll,ll-tetramethyltricyclo[7.2.0.0 ]undecane (3), each isolated in 25% yield. In this tricyclic compound six neighboring asymmetric centers were formed in one step with a very high degree of stereoselectivity. ... 

S-Bromo-8-hydroxy-4,8,ll,ll-tetramethyltricyclo[7.2.0.0 ]undecane (3) Typical Procedure ... 

An alkylidenecyclopropane has been obtained by treating 11-bromo-ll-trimethylsilyltri-cyclo[4.4.1.0 ]undecane with formaldehyde. In another successful synthesis cyclopropyl phenyl sulfone is used as starting material treatment with butyllithium followed by an acylsilane leads to a 1-cyclopropylidene-l-silyloxyalkane 3. ... 

Cl3H14O4, 1,4-Dimethoxybenzocycloheptene-5,9(6H,8H)-dione, 46B, 142 Cl3H,gBr02 f 7-Bromo-4,4-dimethylbicyclo[6.3.0]undecane-2,6-dione, 44B, 147... 

---