Cyclo tetradecane

Dibenzyl-14-crown-4 (lithium ionophore VI 6,6-dibenzyl-l,4,8,ll-tetra-oxa-cyclo-tetradecane) [106868-21-7] M 384.5, m 102-103°. Dissolve in CHCI3, wash with saturated aqueous NaCl, dry with MgSOa, evaporate and purify by chromatography on silica gel and gradient elution with C6Hg-MeOH followed by preparative reverse phase HPLC on an octadecyl silanised silica (ODS) column and eluting with MeOH. It can be crystd from MeOH (v Br 120 cm , C-O-C). [7 Chem Soc Perkin Trans 1 1945 1986.]... 

Dibenzyl-14-crown-4 (lithium ionophore VI, 6,6-dihenzyl-ly4,8,ll-tetra-oxa-cyclo-tetradecane)... 

Cyclohepten 31 mMol in Xylol/ Methanol Hanovia 400 W Vycor-Filter Dimcrc wahr-schoinlich Tri-cyclo[7.5.0.03>Hj tetradecan 20 t 2... 

Table 20 outlines the relative preference of alkyl substituents on the 1,2-tetramethyleneadamantane ring system, and forms the basis for the selection of the C15-C18 saturated stabilomers. Substitution at the 5- and 6-positions was expected to be equivalent and only the former was investigated. The C15H24 saturated co-stabilomers are 1- and ll-methyltetracyclo[7.3.1.P- . 0 ]tct-radecane (these isomers are interconverted by a,e isomerization about the 8-position). AlBrs isomerization studies (52) of CisH24 s showed 40% 1-methyl, 39% 11-methyl, and small amounts (<10%) of 9-methyl (-53.41 (E), -54.44 (A) kcal mole ) and 5- and 6-methyltetracyclo[7.3.1.1 i.o3.8]tetradecane (-53.08 (E), —53.66 (A) kcal mole ) in excellent agreement with the calculations. The C16H26 saturated stabilomer is 1,11-dimethyltetra-cyclo[7.3.1.P ".0 ]tetradecane (Table 11). AlBrs isomerization of Ci6H26 s (52) yielded a mixture of the 1,11-dimethyl derivative (42%) as well as small amounts (<10%) of the 1,9-, 1,6-, 9,11-, 6,11-, 5,11-, and 1,5-dimethyl derivatives.

The Ci7H2s saturated stabilomer is 1,9,11-trimethyltetra-cyclo[7.3.1.P i.o3.8]tetradecane. Model calculations predict the 1,5,11- and 1,6,11-trimethyl derivatives to be less stable but within 1 kcal mole and as such are co-stabilomers. 1,5,9,11- and 1,6,9,1 l-tetramethyltetra-cyclo[7.3.1.P ".0 ]tetradecanes are the CigHso saturated co-stabilomers. 

Dauben and Hart have employed the ring contraction-ring expansion annelation sequence depicted in Scheme 34 to effect the first synthesis of the tri-cyclo[9,3,0,0 ]tetradecane ring system characteristic of the ophiobolin sester-terpenes. ... 

The following aUphatic compounds have been detected in small amounts in Evemia prunastri (L.) Ach. nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, 2-me-thylpentadecane, hexadecane, hepatdecane, pentadec-l-ene, (Z)-heptadeca-l,8-diene, (Z), (Z)-heptadeca-1,8,11 -triene, dec-1 -yne, cyclo-... 

---