Urethanes 1-naphthyl

PHENYL- AND 1-NAPHTHYL-URETHANS (PHENYL- AND 1-NAPHTHYL-CARBAMATES)... 

Phenyl- and a-naphthyl-urethanes (Phenyl- and a-naphthyl-carbamates). Both phenyl isocyanate and a-naphthyl isocyanate react with alcohols to yield phenyl-urethanes and a-naphthyl-urethanes respectively ... 

Preparation of the naph yl-urethane. This compound is prepared in a similar method to that just described, using a-naphthyl-isocyanate. The naphthyl-urethane melts at 53°. 

By oxidation this alcohol yields perillic aldehyde which forms a semi-carbazone, melting at 199° to 200°, and perillic acid, melting at 130° to 131°. It also yields a naphthyl-urethane, melting at 146° to 147°. 

It yields a well-defined phenyl-urethane, melting at 113°. It requires considerable care to obtain this compound, which should be prepared as follows terpineol mixed with the theoretical amount of phenyl-isocyanate is left for four days at the ordinary room temperature. Crystals separate which are diphenyl urea,, and are removed by treating the product with anhydrous ether, in which the diphenyl urea is insoluble. If the liquid be very carefully and slowly evaporated fine needles of terpinyl-phenyl urethane separate. This compound has the formula C Hj. NH. COOCjqHj-. The correspnanding naphthyl-urethane melts at 147° to 148°. 

Alcohol B.P. M.P. 3 S-Dlnltro benzoate benzoate Phenyl urethane a-Naphthyl- urethane Hydrogen i-nltro- phthalate O-Alkyl saccharin Other Derivatives... 

Alcohol B.P. M.P. 3 5-Dlnltro-benzoate p-Nltro- benzoste Phenyl- urethane a-Naphthyl-urethane Hydrogen- 3-nltro- phthalate... 

Alcohol B.P. Benzoate p-Nltro- benzoate 3 5-Dinltro- benzoate Phenyl- urethane a-Naphthyl-urethane Other Derivatives... 

The presence of the naphthyl group of the naphthyl urethane-terminated chains in the polymer obtained with the catalyst containing a naphthyl urethane group was detected by means of UV spectroscopy. Other results obtained indicate the involvement of the monomer nitrogen atom in coordination at the catalyst iron atom. Thus, the coordinating monomer then undergoes an enchainment to yield a urethane function, which may be shown schematically as follows [268] ... 

No Name Melting point "C Boiling point C Phenyl ure- thane a Naphthyl urethane p-Nilro- ben- zoate 3 5-Di nitro benzoaie Bromo derivative P- Toluene sul- fonate Acetate Benzoate Miscellaneous... 

Alcohols (but not ethers) also react with phenyl Mocyanate or with the corresponding crystalline a-naphthyl isocyanate to give carbamates or urethanes (see Section 111,27, ), but these substances are hardly suitable as class reagents. 

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