2- naphthyl myristate

The influence of irradiating 1-naphthyl myristate (1-NM) in LDPE or HDPE is even more dramatic (Table 13.3). In hexane solutions, two photoproducts, 2-myristoyl-l-naphthol and 4-myristoyl-l-naphthol are obtained in a 1.3/1 ratio only one photoproduct, 2-myristoyl-l-naphthol (2-AN), is obtained in unstretched LDPE and HDPE. ... 

Usually, the PFR serves as a probe reaction for the study of the morphology of the matrix. This has been demonstrated by Weiss and co-workers in a series of recent articles on the photoreactivity of esters included in several polyethylene films. Low-density polyethylene (LDPE) films hosting 2-naphthyl esters bring about different selectivity in the PFR as compared with the reaction in solution. In addition, the selectivity is different if the polymer is stretched [286,287], Table 16 indicates the different product distributions upon irradiation of 2-naphthyl esters, depending on the nature of the solvent or matrix. The most striking fact is that irradiation of 2-naphthyl myristate leads to the coupling at the position 1 in ferr-butanol with 86% yield, whereas this product is absent in the irradiations in polyethylene films. Moreover, the product of coupling at position 3 is absent... 

Cui and Weiss reported the photo-Fries rearrangements of 2-naphthyl myristate and 2-naphthyl acetate (Fig. 35) in unstretched and stretched low-density polyethylene films [116]. It was argued that the radical pair generated by irradiation is held in a cavity shaped like the starting ester and whose walls relax more slowly than the radicals recombine. The preferred solution product is too different in shape from the starting ester to be formed. 

For example, irradiation of either 2-naphthyl acetate (2-NA) or 2-naphthyl myristate (2-NM) in the rubbery state of a low density polyethylene (LDPE) or a high density polyethylene (HDPE) yields a variety of in-cage rearrangement products and 2-naphthol (2-NOL), a cage-escape product (Table 13.2). Both LDPE and HDPE consist of amorphous and crystalline regions LDPE has a larger volume... 

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