Characterization of the photoisomers from cis- and trans-chlordanes, trans-nonachlor and heptachlor epoxide

Photolysis of cis-chlordane: identification of two isomers of cis-photochlordane

“…Leaving aside any other structural rearrangements in the molecule, possible photoisomeric forms with cross-links between the dichloroethylene bridge and cyclopentane ring are shown in Figure 1. The spectrum of PC II conforms to the previously published data for PC shown to have a bridge between C2 and C6 (Figure 1,2; Knox et al, 1973).…”

“…The fragment with highest mass appeared at m/e 371 which was due to loss of a chlorine from the molecular ion (M+ -Cl). The remainder of the spectra in all cases were in conformity with previous studies on similar molecules (Benson et al, 1971; Knox et al, 1973;Onuska and Comba, 1975), involving further losses of Cl, HC1, or their com- was present at m/e 373. The similarity of mass spectra in conjunction with identical retention times on GLC columns and closeness of behavior on thin-layer plates (Table II) showed that PC I and PC II were isomeric molecules.…”

“…Study of molecular models of cis-chlordane shows that the carbon C2 is closer to the dichloroethylene bridge than the carbon Cj or C3. Consequently, in cases where such cross-links [for example, structure 4 from cis-chlordane (Lahaniatis et al, 1976) and photoisomers of trans-chlordane and trans-nonachlor which have an endo-chlorine at C2 (Knox et al, 1973)] are formed, yields of the products are lower than we observed in this study. Thus based on the balance of evidence and I T Figure 6.…”

Gas chromatographic determination of several cyclodiene insecticides in the presence of polychlorinated biphenyls by photoisomerization reactions

“…(It is known that irradiation of compounds 4, results in a hydrogen-transfer product (9) which reacts rapidly to compound 8) (Parlar et al, 1975;Knox et al, 1973) (Figure 3).…”

Metabolic fate of cis-photochlordane in the rat. 1. Excretion, tissue distribution, and preliminary characterization of metabolites

“…Benson et al (1971) proposed two alternate configurations of the molecule (Figure 1, II and III) but it was not possible to decide which of the two isomeric forms was produced in their experiments. Knox et al (1973) suggested C2 to C5 bridging (Figure 1, II) in the molecule. More recently, Lahaniatis et al (1976) have indicated that another isomer (Figure 1, IV) involving cross-linking between Cx and C5 is also produced.…”