butylstannane in benzene (1.62 or 3.24 M), and the solutions were degassed, heated at 80 O C for 3 h, and then analyzed for 11 and 12 by GC. The results are given in the text.Reaction of 8 with Tributylstannane. The bromide 8 (10.2 mg, 0.046 mmol) was dissolved in benzene (2.0 mL). Tributylstannane (6.2 pL, 0.023 mmol) and a trace of AIBN were added to an aliquot (0.50 mL) of this solution, which was then heated in a sealed tube at 80 O C for 17 h. After distillation (bath 60 O C (50 mm)), the mixture was analyzed by GC-MS analysis (40 O C isothermal). Varying amounts of tributylstannane were added to other aliquota, which were then heated and analyzed in the same way for 11 and 12. Within experimental error the results obtained were the same as those from reactions of 5. Registry No. HO(CH,),CH(t-BU)(CH~)~CO~M~, 135561-19-2; MeP(Ph)3+.Br-, 1779-49-3; H2C=CHCH2CH(t-Bu)(CH2)2C02Me, 135561-20-5; H02C-(CH2)2CH(t-Bu)CH2C02H, , O~NCBH~COC~, 122-04-3; o-O~NCBHIC(O)O(CH~)~CH(~~U)-(CH2)2OH, 135561-21-6; o-O~NCBHIC(O)O(CH~)~CH(~-BU)-CH,CHO, 135561-22-7; H~C=CHCH~CH(~-BU)CH~C(O)-OC&N02-p, 135561-23-8; N-hydroxypyridine-2-thione, sodium salt, 15922-78-8; 3-tert-butylcyclopentanone, 5581-94-2; l-tertbutyl-3-methylenecyclopentane, 69217-81-8. Supplementary Material Available: Experimental proce-7, 8, intermediates between 6 and 7; and the 0.60.95 ppm region of the " z 1~spectrum of a 32 mixture of cisand trau-12 (9 pages). Ordering information is given on any
