Nor Wahida

Allylisothiocyanateundergoes self-metathesis by 2 nd generation Grubbs catalyst to give 1,4-disothiocyanatobut-ene together with the release of styrene and phosphine ligands. Despite the release of both ligands cross metathesis with methyl oleate, ethyl oleate and ethyl linoleatestill gave some targeted cross and self-metathesis products.1-isothiocyanatoundec-2-ene was detected in all the cross-metathesis reaction. Methyl11-isothiocyanatoundec-9-enoate and ethyl-11-isothiocyanatoundec-9-enoateare products of another cross-metathesis with methyl oleate and ethyl oleate respectively.  Under the reaction conditionno other cross product with ethyl linoleate was detectedexcept the formation of side products ofcarbene species possibly due to side reactions such as isomerization and addition. The formation of 1-isothiocyanatomethylstyreneis the result of the cross metathesis between allylisothiocyanate and styrene. The study indicated that the sulfur atom is more sensitive than oxygen atom...

Cross metathesis (CM) of methyl oleate (MO) with cis-4-octene, cis-stilbene, allyltrimethylsilane by RuCl2(PCy3)(IMesH2)(CHPh) yielded CM products with high MO conversion, high selectivity; the effect of olefin substituents, conditions was explored.

Allylisothiocyanateundergoes self-metathesis by 2 nd generation Grubbs catalyst to give 1,4-disothiocyanatobut-ene together with the release of styrene and phosphine ligands. Despite the release of both ligands cross metathesis with methyl oleate, ethyl oleate and ethyl linoleatestill gave some targeted cross and self-metathesis products.1-isothiocyanatoundec-2-ene was detected in all the cross-metathesis reaction. Methyl11-isothiocyanatoundec-9-enoate and ethyl-11-isothiocyanatoundec-9-enoateare products of another cross-metathesis with methyl oleate and ethyl oleate respectively. Under the reaction conditionno other cross product with ethyl linoleate was detectedexcept the formation of side products ofcarbene species possibly due to side reactions such as isomerization and addition. The formation of 1-isothiocyanatomethylstyreneis the result of the cross metathesis between allylisothiocyanate and styrene. The study indicated that the sulfur atom is more sensitive than oxygen atom to interact with the catalyst resulting in the release of the phosphine and styrene from catalytic cycle. Therefore a suitable protecting agent is necessary to sustain the catalytic cycle.

Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 A ˚ ; R factor = 0.036; wR factor = 0.086; data-to-parameter ratio = 19.6. In the title compound, C 12 H 15 FN 2 O 2 S, the molecule adopts a cis configuration of the fluorobenzoyl group with respect to the thiono group about their C-N bond. The dihedral angle between the fluorobenzoyl group and the thiourea N 2 CS fragment is 69.60 (11). An intramolecular N-HÁ Á ÁO hydrogen bond occurs. In the crystal, molecules form chains along the b-axis direction via O-HÁ Á ÁS and C-HÁ Á ÁO hydrogen bonds. Related literature For bond length data see: Allen et al. (1987). For a related structure, see: Yamin et al. (2014). Experimental Crystal data C 12 H 15 FN 2 O 2 S M r = 270.32 Orthorhombic, P2 1 2 1 2 1 a = 6.0205 (3) A ˚ b = 12.9441 (6) A ˚ c = 17.1071 (9) A ˚ V = 1333.16 (11) A ˚ 3 Z = 4 Mo K radiation = 0.25 mm À1 T = 296 K 0.50 Â 0.50 Â 0.29 mm Data collection Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.885, T max = 0.931 21708 measured reflections 3290 independent reflections 2864 reflections with I > 2(I) R int = 0.031