96 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS H3C02c-•C• (2) H3C02C C02C C02CH 3 (3) i 3 OH (4) [• ': ,C (CO.• 3)2 •...,:,' ß • -. • CH •f'-I-(H3CO3)2H(0020'""'C P-MENTH-L-ENE /:-.... (5) /•-.....(6) (7) CH2CH(CO2CH3)2 b ,.•_ 13-PINENE (8) Scheme 3 a' 12/CH3COOAg/H20 b' dmdm/Cu(acac)2 5.29 ppm (vinyl P-), a neat triplet around 3.51 ppm (malonyl P-), and two dirtbrent singlets at 1.26 and 0.78 ppm (two methylsubstituents attached to the cyclobutane ring). Thus, the structure of 8 was easily identified. As mentioned in the Experimental Table I Proportional Contribution of Dials and Gem-Dimethaxycarbanyl Derivatives in Crude Products (GLC) Terpene Dial reactions % Carben reactions '•-Terpinene (1): 67.6 (2•'3) ß 71 R( + )-p-Menth- 1-ene (4): 65.2 (5•'6) ' 43.9(7):27.9 (IS)-(-) [•-pinene (8) ß 89.1

NEW ODOROUS TERPENES 97 CH3 -CH a OH CH3COCH• • OH (4) OH HaCOCHa , (1) (1 1 ) CH 3 O--•-C O (10) H3 • "•O H (9) Scheme 4 ..O CH 3 (12) section, reaction of terpenes with dmdm was continued until total decomposition of th 'e diazo compound was reached. The absence of dmdm was detected both by GLC and by disappearance of the band at 2130 cm-• in its IR spectrum. Yield of total products after distillation of the excess olefin under reduced pressure was 100% with respect to the exhaustion of dmdm. For this reason, this reaction might have preparative value for production of 8. Compounds 2,3,5,6,7, and 8 also showed pleasant odorous properties that were milder